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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

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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.

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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

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, lipophilic enzymes 9, E-coli

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, viruses

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, 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


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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


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

H, and

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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


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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


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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


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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,

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

Figure S1 and Figure S2.


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


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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).


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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

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.

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


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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.


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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.


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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


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°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


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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


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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)

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New Dendritic Polydiacetylene Sensor with Good ... - ACS Publications

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