New Dendritic Polydiacetylene Sensor with Good Reversible

Subscriber access provided by UB + Fachbibliothek Chemie | (FU-Bibliothekssystem)

Article

A New Dendritic Polydiacetylene Sensor with Good Reversible Thermochromic Ability in Aqueous Solution and Solid Film Wenjie Dong, Guanhua Lin, Haifei Wang, and Wensheng Lu ACS Appl. Mater. Interfaces, Just Accepted Manuscript • DOI: 10.1021/acsami.7b02846 • Publication Date (Web): 15 Mar 2017 Downloaded from http://pubs.acs.org on March 20, 2017

Just Accepted “Just Accepted” manuscripts have been peer-reviewed and accepted for publication. They are posted online prior to technical editing, formatting for publication and author proofing. The American Chemical Society provides “Just Accepted” as a free service to the research community to expedite the dissemination of scientific material as soon as possible after acceptance. “Just Accepted” manuscripts appear in full in PDF format accompanied by an HTML abstract. “Just Accepted” manuscripts have been fully peer reviewed, but should not be considered the official version of record. They are accessible to all readers and citable by the Digital Object Identifier (DOI®). “Just Accepted” is an optional service offered to authors. Therefore, the “Just Accepted” Web site may not include all articles that will be published in the journal. After a manuscript is technically edited and formatted, it will be removed from the “Just Accepted” Web site and published as an ASAP article. Note that technical editing may introduce minor changes to the manuscript text and/or graphics which could affect content, and all legal disclaimers and ethical guidelines that apply to the journal pertain. ACS cannot be held responsible for errors or consequences arising from the use of information contained in these “Just Accepted” manuscripts.

ACS Applied Materials & Interfaces is published by the American Chemical Society. 1155 Sixteenth Street N.W., Washington, DC 20036 Published by American Chemical Society. Copyright © American Chemical Society. However, no copyright claim is made to original U.S. Government works, or works produced by employees of any Commonwealth realm Crown government in the course of their duties.

Page 1 of 22

1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60

ACS Applied Materials & Interfaces

A New Dendritic Polydiacetylene Sensor with Good Reversible Thermochromic Ability in Aqueous Solution and Solid Film Wenjie Dong†, Guanhua Lin†*，Haifei Wang, and Wensheng Lu

Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Colloid and Surface Science, Institute of Chemistry, Chinese Academy of Science, Beijing 100190, P. R. China. Corresponding Email: [email protected] KEY WORDS: Polydiacetylene; sensor; revesible, thermochromic; film. ABSTRACT Thermal responsive polydiacetylene derived from PAMAM dendrimer (PDA-G0) was synthesized. Unlike the ethylenediamine substituted PDA (PDA-NH2) solution, the prepared PDA-G0 vesicle solution showed reversible thermochromism property when temperature varied from 20 oC to 90 oC, which is due to formation of internal hydrogen-bond in amide groups. Furthermore, PDA-G0/PMMA film with excellent stability was obtained by a mixed-drying method, which could be stored for a long time without denaturation. After polymerization by UV irradiation, it displayed much better reversible thermochromic ability and the responded temperature range became wider, from 20 oC to110 oC.

ACS Paragon Plus Environment

1


1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60

Page 2 of 22

INTRODUCTION Conjugated polymers with delocalized π-network and conformationally restricted structure have been widely used in chemosensor field due to their obvious changes in absorption and emission when disturbed by environmental stimuli. Among these conjugated polymers, polydiacetylene (PDA) is particularly attractive because of its color change property related with external stimuli. When exposed to external stimuli: temperature 1-3, pH 4-6 or biomolecules such as proteins compounds

7,8

13

, lipophilic enzymes 9, E-coli

10

, viruses

11,12

, and pharmacologically active

, PDA undergoes an obvious naked color change (changes from blue to red with

the dramatic shift of absorption λmax from about 650 nm to 540 nm) and a fluorescence transition from nonfluorescent to fluorescent. Therefore, PDA-based sensor has been developed as colorimetric sensor device in chemical, and biological field

14-16

, such as they present excellent

applications in food safety and detection of bacteria 17,18. Usually, PDA can be obtained via a 1, 4-addition of diacetylene (DA) monomer under γ irradiation, then it appears intense blue color which present absorption peak at approximately 650 nm due to the alternating of ene-yne backbone 19,20. Traditionally, most of the PDA sensors exhibited an irreversibility in their chromatic change, and thus, their direct applications are limited as they cannot provide a cyclic response. During practical application process, sustainable detecting and recover ability and stability is essential, so excellent reversible ability is one of the key factors to act as a good sensors. To achieve reversible colorimetrictransition, various chemical modiﬁcations were introduced into diacetylenes to enhance the attractive intramolecular interaction among their head groups in side chains

21-25

. And it is reported that

inorganic ions also could help to form reversible thermochromic PDA nanocomposites 26. So far, some efforts have been made on developing the PDA based sensor with good reversibility in


2

Page 3 of 22

1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60


chromatic change 27-29, for example PDA based sensor with thermochromic reversibility has been prepared 30. PDA-based sensors could be prepared in various forms, including vesicles Blodgett (LB) or Langmuir–Schaefer (LS) film encapsulated in different matrixes

33-36

32

31

, Langmuir–

and other forms where PDA vesicles are

. PAMAM dendrimers are hyperbranched polymers with

unparalleled molecular uniformity, with good advantage of narrow molecular weight distribution, defined size and shape characteristics and placement of functional groups, which are desirable for many life science applications37. Also, they could be considered as good supporting matrix to immobilize other molecules38. In this paper, we prepared a new kind of dendritic PDA derivative: PDA-G0, and studied its thermal reversible performance in aqueous solution and in solid phase. We found that the PDA-G0 vesicle solution showed good thermal reversible property between 20 °C and 90 °C. More interestingly, the PDA-G0 embedded PMMA film possess wider thermal reversible range from 20 °C to 110 °C, and better stability which can be stored for several months without color change. Our results proved that PDA-G0 could be used as good thermal reversible material, which present excellent practical applications in the field of sensor. EXPERIMENTIAL SECTION Materials 98 % pure 10, 12-pentacosadiynoic acid (PCDA) was purchased from Sigma-Aldrich Co., and was further purified before use by dissolution in chloroform followed by filtration to remove polymerized monomers. N-hydroxysuccinimide (NHS), 1-(3-(dimethylamino) propyl)-3ethylcarbodiimide hydrochloride (EDC) and 1-Hydroxybenzotriazole (HOBT) were purchased from Sigma-Aldrich. N-(tert-Butoxycarbonyl)ethylenediamine (≥97%) was purchased from


3


1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60

Page 4 of 22

Aladdin Industrial Inc. Solvents and other reagents were obtained from Beijing Chemical Plant. 1

H, and

13

C NMR spectra were recorded on a Bruker Model Avance DMX 300 or 600

Spectrometer (1H 300 MHz, 400 MHz and 13C 75 or 150 MHz, respectively). MALDI-TOF mass spectra were obtained on a BIFLEX Ⅲ instrument with α-cyano-4-hydroxycinnamic acid (CCA) as the matrix. Synthesis of PCDA-NH2 10,12-pentacosadiynoic acid 2-aminoethylamide (PCDA–NH2) was synthesized according to the procedure in literature 39. Michael addition step: PCDA-G-0.5: A solution of PCDA-NH2 (1.0 g, 2.4 mmol) in mixture of dichloromethane and methanol (1:1, v/v, 30 mL) was added to methylacrylate (10 mL, 120 mmol), and the resulting mixture was stirred for 5 days at room temperature upon the completion of the reaction. Then the solvent was removed under reduced pressure. The product was obtained as a pale yellow solid (1.3 g, 92 %) 1

H NMR (400MHz, CDCl3) δ (ppm): 0.86-0.90 (t, 3H, J=6.80 Hz), 1.26-1.65 (m, 33H), 2.17-

2.75 (m, 6H), 2.41-2.44 (t, 4H, J=6.40 Hz), 2.51-2.53 (t, 2H, J=5.40 Hz), 2.72-2.75 (t, 4H, J=6.60 Hz), 3.30-3.33 (m, 2H), 3.68(s, 6H), 6.46(s, 1H) MS (MALDI-TOF): C35H60N2O5 m/z calcd for [M+H] +:589.5; found: 589.3. Amidation step: PCDA-G0: A solution of PCDA- G-0.5 (1.0 g 1.7 mmol) in mixture of dichloromethane and methanol (1:1, v/v, 30 ml) was added to ethylenediamine (6 mL 84.9 mmol) and stirred for 7 days at room temperature upon the completion of the reaction. After the reaction, most solvent was removed under reduced pressure. The obtained residue was further


4

Page 5 of 22

1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60


purified by precipitation into mixture of n-hexane and ether for at least three times. The product was obtained as a pale yellow solid (1.06 g, 97 %) 1

H NMR (300MHz, CDCl3) δ (ppm): 0.84-0.89 (t, 3H, J=6.45 Hz), 1.24-1.58 (m, 32H), 2.13-

2.24 (m, 6H), 2.36 (br s, 4H), 2.53 (br s, 2H), 2.72 (br s, 4H), 2.90-2.92 (m, 4H), 3.27-3.33 (m, 6H), 3.81-3.89 (br s, 6H), 7.38 (br s, 1H), 7.77 (br s,2H) 13

C NMR (150 MHz, CDCl3) δ (ppm):174.22, 173.63, 77.69, 77.37, 77.16, 76.95, 65.42, 65.34,

52.89, 52.67, 50.39, 50.21, 42.43, 41.22, 40.94, 40.80, 40.51, 38.62, 37.87, 36.56, 34.18, 31.99, 29.70, 29.56, 29.47, 29.41, 29.18, 29.11, 28.96, 28.46, 25.95, 22.76, 19.28, 14.20 MS (MALDI-TOF): C37H68N6O8 m/z calcd for [M+Na]+: 667.5; found: 667.7. Preparation of PCDA vesicles 5 mL of 1 mM PCDA suspension dissolved in chloroform was rotoevaporated to dry, and then the same amount of phosphate buffered saline (PBS, pH=7.2) solution was added to keep the lipid concentration. The suspension was sonicated in an ultrasonicator bath (KQ-100B ultrasonicator, Kunshan Ultrasonic Instrument Co., Shanghai, China) for about 20 mins in 80 °C ，and then probe sonicated for approximately 6 mins. After sonication, the suspension was cooled to room temperature and stored overnight at 4 °C to induce crystallization of lipid membranes. Fabrication of PDA-G0/PMMA Film


5


1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60

Page 6 of 22

A chloroform solution of PCDA-G0 (1 mM, 2 mL) was mixed with PMMA (0.5 g). The solution was casted into a watch glass as a mold and dried at room temperature for a week. Being irradiated with 254 nm UV light (40 W) for five seconds, the blue film was obtained. Chromatic detection The thermochromism property of the film was monitored by HITACHI U-2800 UV spectrometer while the temperature increases from 20 °C to 90 °C (10 mins), then cooling to 20 °C as a thermal cycle. The extent of a color transition was quantitatively measured by colorimetric response (CR), which is defined as follows:

% CR =

100 × ( PB0 − PB) PB0

PB =Ablue/(Ablue + Ared), and Ablue and Ared are the absorbances of the blue component (λmax ≈ 650 nm) and the red component (λmax ≈ 540 nm) respectively. PB0 is the initial percentage of the blue component before adding the analyte. RESULTS AND DISCUSSION Synthesis of Diacetylene Monomers In the synthesis of chemicals, selecting an appropriate route is the key to obtain high purity and yielding of products. There are two main factors should be considered during synthesis of diacetylene, one is that diacetylene readily undergo polymerization after exposed to light for a long time, the other is that purification of amphiphilic dendrimers by column chromatography is


6

Page 7 of 22

1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60


tedious for its complicated process. Based on the above two reasons, we chose a convenient and highly efficient way to prepare the diacetylene derivatives. The PCDA-NH2 was fabricated as a typical method, shown in Figure 1a. It could be seen that PCDA-NH2 was prepared by a NHS-EDC reaction of PCDA with suitable amine, and having a good yielding (about 90 %). Then, the as-prepared PCDA-NH2, as the main reactants, was used to fabricate dendrimer PCDA-G0 via the divergent method which was usually used in the preparation of Tomalia-type PAMAM dendrons

40

. Figure 1b and Figure 1c present the detail

synthetic routes of dendrimer PCDA-G0, firstly the obtained PCDA-NH2 was added into overdoes of methylacrylate, which was used as the growth unit for Michael addition. Then, followed by an amidation reaction, overdoes of ethylenediamine reacted with the as-prepared dendritic ester (PCDA-G0.5) to fabricate PCDA-G0 with good yielding. The obtained products were analyzed by 1H NMR,

13

C NMR and TOF mass spectrometry, which were shown in the

Figure S1 and Figure S2.


7


1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60

Page 8 of 22

Figure 1. Synthesis of diacetylene derivatives: the synthetic route for (a) PCDA-NH2; (b) PCDA-G-0.5; (c) PCDA-G0.


8

Page 9 of 22

1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60


Figure 2. (a) UV-vis spectra of the PDA-NH2 solution at 20 °C (black curve), 90 °C (blue curve) and cooling back to 20 °C (red curve). (b) UV-vis spectra of the PCDA-G0 solution during the heating process from 20 to 90 °C; (c) UV-vis spectra of the PCDA-G0 solution during the cooling process from 90 to 20 °C (the photographs in the upper left corner and the upper right corner are the solution at 90 °C and 20 °C, respectively).


9


1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60

Page 10 of 22

Figure 3. Colorimetric response (CR) values of PCDA-G0solution during heating and cooling cycles between 20 °C and 90 °C. Thermochromism of polydiacetylene polymer in solution In order to investigate the thermochromism of them, as-prepared two kinds of monomers were transformed into polydiacetylene (PDA) structures by ultrasonicating each monomers in Milli-Q water and followed by irradiating with UV light. The color of PDA-NH2 solution varied from blue to red with the increase of temperature from 20 °C to 90 °C, and retained to red when temperature cooled back to 20 °C. It means that PDA-NH2 solution present thermal irreversibility. Details can be seen from Figure 2a, the maximum absorption peak of PDA-NH2 solution appeared at 540 nm at 90 °C. Even if lowering the temperature back to 20 °C, it still stay at 540 nm instead of returning back to 640 nm. It is reported that internal hydrogen-bondable amide groups played a significant role in governing the reversibility of the color change

41

.

However, there is only one amido bond in PDA-NH2 monomer and they prefer forming


10

Page 11 of 22

1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60


intermolecular hydrogen bond than intramolecular hydrogen bond, which is unable to induce thermal reversibility. Compared with the PDA-NH2 solution, PDA-G0 solution displayed good thermal reversibility, as shown in Figure 2b and Figure 2c. As temperature increased from 20 °C to 90 °C, the color of solution changed from blue to red gradually, accompanied by decrease of absorption at about 614 nm and increase of absorption at 540 nm at the same time. Upon backing to the initial temperature, the color of the PDA-G0 solution would return back to blue too. We believed that the abundant amido groups in PDA-G0 molecules and branched molecular structures of PDA-G0 provided strong support for them in forming intramolecular hydrogen bond, which were able to generate thermal reversibility of PDA-G0 solution. The representative percentage colorimetric response values (CR %), calculated from the relevant UV-vis spectrum, could well quantify their degree of thermal reversibility. In Figure 3, the CR value is calculated from six cycles of heating and cooling between 20 °C and 90 °C, which confirmed that the PDAG0 solution possessed excellent thermochromic reversibility. Compared with previous PDA sensor, the PDA-G0 vesicles have wider range of reversible temperature and higher colorimetric response value.


11


1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60

Page 12 of 22

Figure 4. (A) Schematically present the preparation process of PDA-G0/PMMA film. (B) Photographs revealing the polymerization of the colorless PCDA-G0/PMMA film and the reversible thermochromism for the polymerized ﬁlm (PDA-G0/PMMA) between 20 °C and 110 °C.


12

Page 13 of 22

1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60


Figure 5. (a) UV-vis spectra of the PDA-G0/PMMA film during the heating process from 20 °C to 110 °C; (b) UV-vis spectra of the PDA-G0/PMMA film during the cooling process from 110


13


1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60

Page 14 of 22

°C to 20 °C; (c) colorimetric response (CR) changes in 20 thermal cycles between 20 °C and 110 °C. Thermochromism of PDA-G0/PMMA film As discussed above, PDA-G0 solution possess good thermal reversibility when temperature varied from 20 °C to 90 °C. To further explore the application of PDA-G0, we investigated the thermal reversibility of PDA-G0 in solid phase. PMMA, is a well-known and widely-used plexiglass due to its good transparency, chemical stability and weathering resistance. Here, PMMA was used as matrix to prepare PDA-G0/PMMA film by a mixed-drying process (Figure 4a). The as-prepared PDA-G0/PMMA film was stable and could be stored for several months without color change. Most notably, the film present better thermal reversibility than that of solution. As shown in Figure 4b, the colorless and transparent film transformed into blue color under UV light irradiating for several seconds at room temperature of 20 °C and gradually turned to red with the temperature increasing to 110 °C. When cooled back to the room temperature, the film completely recovered to blue color. The reversible thermochromism of the film was clearly proved by UV-vis measurements between 20 °C and 110 °C. As shown in Figure 5a, when the film in blue color, a maximum absorption appeared at about 640 nm during 20 °C. Once the temperature increasing gradually, the maximum absorption continuously shifted to shorter wavelengths with absorption peaks at 540 nm. Up to 110 °C, the absorption peak at about 640 nm completely disappeared, but the maximum absorption peak strongly present at 540 nm, which was responsible for the red color. Upon cooling, the absorption spectrum changed inversely as shown in Figure 5b. Meanwhile, the whole “heating-cooling” cycles between 20 °C and 110 °C confirmed their good reversible thermochromic ability. As shown in Figure 5c, even during 20th “heating-cooling” cycles, the CR value at 110 °C remained at about 70 %. There was


14

Page 15 of 22

1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60


a video (Movie S3) shown the film’s reversible color change process from blue color changed to red color and then returned back to blue color, when the temperature was gradually cooled from 110 °C to 20 °C. The color change of the film was quite quickly, it could be seen the red film changed to blue (supporting information, Movie S3) within 1 min, which means the film is very sensitive to the changing of temperature and possess excellent potential application as sensor. In a word, the PDA-G0 film has wider reversible thermochromic temperature range than that of in the solution. And the PDA-G0 film shows quite strong and flexible, there was no any damage after being used so many times. Now, we are unclear why PDA- G0 in solid phase has wider reversible temperature range, but not hinder its practical significant for future applications. CONCLUSION In conclusion, a new kind of dendritic PCDA derivatives (PCDA-G0) was synthesized and provided a new approach for the preparation of PDA derivatives. Meanwhile, the study of thermochromic behavior shows that compared with PDA-NH2 solution, PDA-G0 solution displayed a better thermochromic reversibility during 20 °C to 90 °C. Our results confirmed that internal hydrogen-bondable amide groups played an important role in the reversible thermal color change. Moreover, the PDA-G0 shows substantially reversible thermochromic behavior both in solution and solid phase, but solid phase possess wider temperature range between 20 °C to 110 °C. Significantly, the PDA-G0/PMMA film presents potential applications in the field of thermal sensor and our method will be a typical example in developing simple, fast detecting and sustainable sensors. And we believed our method will be useful in fabricating other kinds of sensors. ASSOCIATED CONTENT


15


1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60

Page 16 of 22

Supporting Information. PCDA-G0 products were analyzed by 1H NMR, 13C NMR and TOF mass spectrometry, and video (Movie S3) about the PDA-G0/PMMA film color change, all these data could be obtained from http://pubs.acs.org. AUTHOR INFORMATION Corresponding Author Dr. Guanhua Lin. Email: [email protected] Author Contributions † Wenjie Dong and Guanhua Lin contributed equally to this paper. ACKNOWLEDGMENT The authors would like to acknowledge funding from the National Natural Science Foundation of China (Grant Nos. 20903106, 20933007, 91127012, 21161130521, 21321063)

REFERENCES

(1) Ahn, D. J.; Chae, E.-H.; Lee, G. S.; Shim, H.-Y.; Chang, T.-E.; Ahn, K.-D.; Kim, J.-M. Colorimetric Reversibility of Polydiacetylene Supramolecules Having Enhanced HydrogenBonding under Thermal and pH Stimuli. J. Am. Chem. Soc. 2003, 125, 8976-8977. (2) Peng, H.; Tang, J.; Yang, L.; Pang, J.; Ashbaugh, H. S.; Brinker, C. J.; Yang, Z.; Lu, Y. Responsive Periodic Mesoporous Polydiacetylene/Silica Nanocomposites. J. Am. Chem. Soc. 2006, 128, 5304-5305. (3) Singh, A.; Thompson, R. B.; Schnur, J. M. Reversible Thermochromism in Photopolymerized Phosphatidylcholine Vesicles. J. Am. Chem. Soc. 1986, 108, 2785-2787.


16

Page 17 of 22

1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60


(4) Jonas, U.; Shah, K.; Norvez, S.; Charych, D. H. Reversible Color Switching and Unusual Solution Polymerization of Hydrazide-Modified Diacetylene Lipids. J. Am. Chem. Soc. 1999, 121, 4580-4588. (5) Song, J.; Cheng, Q.; Kopta, S.; Stevens, R. C. Modulating Artificial Membrane Morphology: pH-Induced Chromatic Transition and Nanostructural Transformation of a Bolaamphiphilic Conjugated Polymer from Blue Helical Ribbons to Red Nanofibers. J. Am. Chem. Soc. 2001, 123, 3205-3213. (6) Kew, S. J.; Hall, E. A. H. pH Response of Carboxy-Terminated Colorimetric Polydiacetylene Vesicles. Anal. Chem. 2006, 78, 2231-2238. (7) Cornell, B. A.; Braach-Maksvytis, V. L. B.; King, L. G.; Osman, P. D. J.; Raguse, B.; Wieczorek, L.; Pace, R. J. A Biosensor that Uses Ion-Channel Switches. Nature 1997, 387, 580-583. (8) Trester-Zedlitz, M.; Kamada, K.; Burley, S. K.; Fenyö, D.; Chait, B. T.; Muir, T. W. A Modular Cross-Linking Approach for Exploring Protein Interactions. J. Am. Chem. Soc. 2003, 125, 2416-2425. (9) Jelinek, R.; Okada, S.; Norvez, S.; Charych, D. Interfacial Catalysis by Phospholipases at Conjugated Lipid Vesicles: Colorimetric Detection and NMR Spectroscopy. Chem. Biol.1998, 5, 619-629. (10) Ma, Z.; Li, J.; Liu, M.; Cao, J.; Zou, Z.; Tu, J.; Jiang, L. Colorimetric Detection of Escherichia coli by Polydiacetylene Vesicles Functionalized with Glycolipid. J. Am. Chem. Soc. 1998, 120, 12678-12679.


17


1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60

Page 18 of 22

(11) Reichert, A.; Nagy, J. O.; Spevak, W.; Charych, D. Polydiacetylene Liposomes Functionalized with Sialic Acid Bind and Colorimetrically Detect Influenza Virus. J. Am. Chem. Soc. 1995, 117, 829-830. (12) Deng, J.; Sheng, Z.; Zhou, K.; Duan, M.; Yu, C.-y.; Jiang, L. Construction of Effective Receptor for Recognition of Avian Influenza H5N1 Protein HA1 by Assembly of Monohead Glycolipids on Polydiacetylene Vesicle Surface. Bioconjugate Chem. 2009, 20, 533-537. (13) Jelinek, R.; Kolusheva, S. Polymerized Lipid Vesicles as Colorimetric Biosensors for Biotechnological Applications. Biotechnol. Adv. 2001, 19, 109-118. (14) Dolai, S.; Bhunia, S. K.; Beglaryan, S. S.; Kolusheva, S.; Zeiri, L.; Jelinek, R. Colorimetric Polydiacetylene–Aerogel Detector for Volatile Organic Compounds (VOCs). ACS Appl. Mater. Interfaces 2017, 9, 2891-2898. (15) Lee, S.; Kim, J.-Y.; Chen, X.; Yoon, J. Recent Progress in Stimuli-Induced Polydiacetylenes for Sensing Temperature, Chemical and Biological Targets. Chem. Commun. 2016, 52, 9178-9196. (16) Wang, F.; Wang, L.; Chen, X.; Yoon, J. Recent Progress in the Development of Fluorometric and Colorimetric Chemosensors for Detection of Cyanide Ions. Chem. Soc. Rev. 2014, 43, 4312-4324. (17) de Oliveira, T. V.; Soares, N. d. F. F.; Coimbra, J. S. d. R.; de Andrade, N. J.; Moura, L. G.; Medeiros, E. A. A.; de Medeiros, H. S. Stability and Sensitivity of Polydiacetylene Vesicles to Detect Salmonella. Sens. Actuators, B 2015, 221, 653-658.


18

Page 19 of 22

1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60


(18) Zhang, Y.; Northcutt, J.; Hanks, T.; Miller, I.; Pennington, B.; Jelinek, R.; Han, I.; Dawson, P. Polydiacetylene Sensor Interaction with Food Sanitizers and Surfactants. Food Chem. 2017, 221, 515-520. (19) Chen, X.; Zhou, G.; Peng, X.; Yoon, J. Biosensors and Chemosensors Based on the Optical Responses of Polydiacetylenes. Chem. Soc. Rev. 2012, 41, 4610-4630. (20) Jelinek, R.; Ritenberg, M. Polydiacetylenes-Recent Molecular Advances and Applications. RSC Adv. 2013, 3, 21192-21201. (21) Peng, H.; Tang, J.; Pang, J.; Chen, D.; Yang, L.; Ashbaugh, H. S.; Brinker, C. J.; Yang, Z.; Lu, Y. Polydiacetylene/Silica Nanocomposites with Tunable Mesostructure and Thermochromatism from Diacetylenic Assembling Molecules. J. Am. Chem. Soc. 2005, 127, 12782-12783. (22) Ryu, S.; Yoo, I.; Song, S.; Yoon, B.; Kim, J.-M. A Thermoresponsive Fluorogenic Conjugated Polymer for a Temperature Sensor in Microfluidic Devices. J. Am. Chem. Soc. 2009, 131, 3800-3801. (23) Phollookin, C.; Wacharasindhu, S.; Ajavakom, A.; Tumcharern, G.; Ampornpun, S.; Eaidkong, T.; Sukwattanasinitt, M. Tuning Down of Color Transition Temperature of Thermochromically Reversible Bisdiynamide Polydiacetylenes. Macromolecules 2010, 43, 7540-7548. (24) Chen, X.; Yoon, J. A thermally Reversible Temperature Sensor Based on Polydiacetylene: Synthesis and Thermochromic Properties. Dyes Pigm. 2011, 89, 194-198. (25) Palladino, P.; Castelletto, V.; Dehsorkhi, A.; Stetsenko, D.; Hamley, I. W. Reversible Thermal Transition of Polydiacetylene Based on KTTKS Collagen Sequence. Chem. Commun. 2012, 48, 9774-9776.


19


1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60

Page 20 of 22

(26) Traiphol, N.; Chanakul, A.; Kamphan, A.; Traiphol, R. Role of Zn2+ Ion on the Formation of Reversible Thermochromic Polydiacetylene/Zinc Oxide Nanocomposites. Thin Solid Films 2017, 622, 122-129. (27) Lee, S.; Lee, J.; Kim, H. N.; Kim, M. H.; Yoon, J. Thermally Reversible Polydiacetylenes Derived from Ethylene Oxide-Containing Bisdiacetylenes. Sens. Actuators B, 2012, 173, 419-425. (28) Chanakul, A.; Traiphol, N.; Traiphol, R. Controlling the Reversible Thermochromism of Polydiacetylene/Zinc Oxide Nanocomposites by Varying Alkyl Chain Length. J. Colloid Interface Sci. 2013, 389, 106-114. (29) Shin, M. J.; Kim, J.-D. Reversible Chromatic Response of Polydiacetylene Derivative Vesicles in D2O Solvent. Langmuir 2016, 32, 882-888. (30) Lee, S.; Lee, J.; Lee, M.; Cho, Y. K.; Baek, J.; Kim, J.; Park, S.; Kim, M. H.; Chang, R.; Yoon, J. Construction and Molecular Understanding of an Unprecedented, Reversibly Thermochromic Bis-Polydiacetylene. Adv. Funct. Mater. 2014, 24, 3699-3705. (31) Su, Y.-l.; Li, J.-r.; Jiang, L.; Cao, J. Biosensor Signal Amplification of Vesicles Functionalized with Glycolipid for Colorimetric Detection of Escherichia Coli. J. Colloid Interface Sci. 2005, 284, 114-119. (32) Cabaj, J.; Soloducho, J.; Jedrychowska, A.; Zajac, D. Biosensing Invertase-Based Langmuir-Schaefer Films: Preparation and Characteristic. Sens. Actuators B, 2012, s 16667, 75-82. (33) Yamanaka, S. A.; Charych, D. H.; Loy, D. A.; Sasaki, D. Y. Solid Phase Immobilization of Optically Responsive Liposomes in Sol-Gel Materials for Chemical and Biological Sensing. Langmuir 1997, 13, 5049-5053.


20

Page 21 of 22

1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60


(34) Gu, Y.; Cao, W.; Zhu, L.; Chen, D.; Jiang, M. Polymer Mortar Assisted Self-Assembly of Nanocrystalline Polydiacetylene Bricks Showing Reversible Thermochromism. Macromolecules 2008, 41, 2299-2303. (35) Yoon, B.; Shin, H.; Kang, E.-M.; Cho, D. W.; Shin, K.; Chung, H.; Lee, C. W.; Kim, J.-M. Inkjet-Compatible Single-Component Polydiacetylene Precursors for Thermochromic Paper Sensors. ACS Appl. Mater. Interfaces 2013, 5, 4527-4535. (36) Kamphan, A.; Traiphol, N.; Traiphol, R. Versatile Route to Prepare Reversible Thermochromic

Polydiacetylene

Nanocomposite

Using

Low

Molecular

Weight

Poly(vinylpyrrolidone). Colloids Surf., A 2016, 497, 370-377. (37) Tomalia, D. A.; Baker, H.; Dewald, J.; Hall, M.; Kallos, G.; Martin, S.; Roeck, J.; Ryder, J.; Smith, P. Dendritic Macromolecules: Synthesis of Starburst Dendrimers. Macromolecules 1986, 19, 2466-2468. (38) Crepaldi, L. B.; Neto, S. A.; Cardoso, F. P.; Ciancaglini, P.; De Andrade, A. R. Ferrocene Entrapped In Polypyrrole Film and PAMAM Dendrimers as Matrix for Mediated Glucose/O2 Biofuel Cell. Electrochim. Acta 2014, 136, 52-58. (39) Bruehl, R. E.; Dasgupta, F.; Katsumoto, T. R.; Tan, J. H.; Bertozzi, C. R.; Spevak, W.; Ahn, D. J.; Rosen, S. D.; Nagy, J. O. Polymerized Liposome Assemblies: Bifunctional Macromolecular Selectin Inhibitors Mimicking Physiological Selectin Ligands. Biochem. 2001, 40, 5964-5974. (40) Liu, J.; Feng, Y.; He, Y.; Yang, N.; Fan, Q.-H. Janus Dendritic Phosphines: Synthesis and Application in Suzuki Coupling Reactions. New J. Chem. 2012, 36, 380-385. (41) Lee, S.; Kim, J.-M. α-Cyclodextrin: A Molecule for Testing Colorimetric Reversibility of Polydiacetylene Supramolecules. Macromolecules 2007, 40, 9201-9204.


21


1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60

Page 22 of 22

TOC.


22

New Dendritic Polydiacetylene Sensor with Good Reversible

Recommend Documents