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Tunable Supramolecular Helical Aggregate and Optoelectrical Properties of Perylene Diimides by Stereoisomerism of Sugar Xiaotian Liu, Zhijian Huang, Yongwei Huang, Lingyun Zhu, and Ji-Ya Fu J. Phys. Chem. C, Just Accepted Manuscript • DOI: 10.1021/acs.jpcc.7b02014 • Publication Date (Web): 13 Mar 2017 Downloaded from http://pubs.acs.org on March 20, 2017

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The Journal of Physical Chemistry

Tunable Supramolecular Helical Aggregate and Optoelectrical Properties of Perylene Diimides by Stereoisomerism of Sugar

Xiaotian Liu,1,2 Zhijian Huang,1 Yongwei Huang,*2 Lingyu Zhu,*3 and Jiya Fu*1

1

Henan Engineering Laboratory of Flame-Retardantand Functional Materials, College of

Chemistry and Chemical Engineering, Henan University, Kaifeng, 475004, China 2

Laboratory for Medical Nanomaterials, School of Basic Medical Science, Henan

University, Kaifeng 475004, China 3

National Centre for Nanoscience and Technology, Beijing 100090, China

Corresponding authors: E-mail: [email protected] (Huang, Y.), [email protected] (Fu, J.), [email protected] (Zhu, L.)

1

ACS Paragon Plus Environment


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ABSTRACT In the present study, two sugar-based perylenediimide derivatives (PDIs) substituted at imide positions with carbohydrate groups were synthesized to investigate the impact of stereoisomerism of sugar on aggregation morphologies and optoelectrical properties. Results showed the right-handed and left-handed helical nanowire fibers for α-D-glucopyranoside and β-D-glucopyranoside-substituted PDIs, respectively, were obtained in tetrahydrofuran (THF) / H2O solution. Determination of electrical current in hydrazine vapor revealed that both sugar-based chiral PDIs exhibited more enhanced current changes relative to their achiral counterparts due to larger π-π orbital overlap between adjacent perylene cores. A larger π-π orbital overlap and a smaller π-π interplanar spacing more remarkably increased electrical current

of

α-D-glucopyranoside-substituted

PDIs

compared

with

β-D-glucopyranoside-substituted ones. Results of this study suggest that stereoisomerism of chiral sugar groups significantly influence aggregation morphology and optoelectrical properties of PDIs by adjusting intermolecular interactions, π-π overlap, and π-π distance.

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INTRODUCTION Perylene-3,4,9,10-tetracarboxyldiimides (PDIs) are a class of organic semiconductor materials that are widely applied in organic optoelectrical devices and biological fields.1−5 Findings of relationships between PDIs molecular structures and their optoelectrical properties is conducive to the further development of PDIs with optimal performance. Some studies indicated that aggregated morphologies and optoelectrical properties could be adjusted by intermolecular interactions (e.g., π–π stacking and π–π overlap).2,3 For instance, introduction of substituted groups to the imide positions or bay regions of perylene core can well tune the morphologies and optoelectric properties of PDIs materials.6−14 Especially, the incorporation of chiral group on the imide position(s) can modulate the self-assembly behaviours of PDIs by changing the molecular interactions that generated by the spatially specific steric hindrance of the chiral group.15-18 On one hand, the chirality of substituted groups can be expressed in supramolecular architectures and lead to the formation of helical nanostructures. On the other hand, chiral substituents can offer additional noncovalent interactions, thus affecting the packing distance, and optoelectronic properties.19

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Carbohydrates exist widely in nature, which can be used to produce helical aggregations because of their spatially specific steric hindrance that roots in inherent chiral centers.20-23 In recent, sugar-based PDIs are of great interest because of their potential application in optoelectrical materials,24,25 switchable interfaces,26 and carbohydrate−protein interactions.27,28

Studies revealed solvents can be used to

tune

the helical aggregation morphologies of α-D-glucopyranoside-substituted PDIs.25,27 In more recent studies, we further prepared some β-D-glucopyranoside-substituted PDIs and found that substituted groups in the imide and bay regions could well modulate their self-assembled behaviors.21,25 As known that stereoisomerism of sugar affects aggregation behaviours of perylene molecules have not been systematically compared and unveiled. Moreover, we found that stereoisomerism of chiral alkyl chain in the bay regions can well enhanced current changes of PDIs compare with the achiral counterparts in sensing devices.10 These interesting results motivate us to conduct further investigation to understand the chirality and stereoisomerism of sugar how to affect supramolecular helical aggregation and optoelectrical properties of perylene molecules.

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In this present study, we prepared two new perylenediimide derivatives that bear sugar

groups

at

the

imide

N

postions:

N,

N′-bis[(4-aminophenyl)-α-D-glucopyranoside)-1,6,7,12-tetra-(4′-(1′′,1′′,3′′,3′′-tetramethylbutyl)-phenoxy)]-perylene-3,4:9,10-tetracarboxyldi-imide

(a)

and

N,N′-bis[(4-amino-phenyl)-β-D-glucopyranoside)-1,6,7,12-tetra-(4′-(1′′,1′′,3′′,3′′-tetrame thyl-butyl)phenolxy)]-perylene-3,4:9,10-tetracarboxyldiimide (b, Scheme 1).

Different

from our previous report, more emphases in current study are placed on the effect of stereoisomerism of sugar, namely α and β stereostructure, on the modulating of helical supramolecular aggregation and optoelectrical properties. Moreover, for comparison purpose,

N,

N’-bis(4-methylphenyl)-1,6,7,12-tetra

tetramethylbutyl)phenoxy))-perylene-3,4:9,10-tetracarboxyldiimide

(4’-(1′′,1′′,3′′,3′′(c,

Scheme

1)

without sugar-substituted group was also synthesized. Findings revealed aggregation morphologies and optoelectrical properties are highly influenced by stereoisomerism of sugar. We hope that this research can present an elaborated method to modulate helical aggregation and optoelectrical properties by stereoisomerism of chiral substituted groups.

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EXPERIMENTAL SECTION Circular dichroism (CD) determinations were performed on a JASCOJ-810 spectrometer. Perkin-Elmer Lamda 950 UV-vis spectroscopy had been used to record UV-vis adsorption spectra. Morphologies of nanostructure were acquired on a field-emission scanning electron microscopy (SEM, Hitachi S-4800, 5 kV). Transmission electron microscopy (TEM) morphologies were acquired on a TECHNAI G2 20 S-TWIN (200 KV). Proton nuclear magnetic resonance (NMR) and

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C NMR were conducted by a Bruker 400 MHz NMR

spectrometer. A Rigaku D/max-2500 rotation anode X-ray diffractometer was used to record X-ray diffraction (XRD) patterns (graphite monochromatized Cu Kα radiation, λ = 1.5418 Å). Theoretical calculation was finished using the density functional theory (DFT) with B3LYP-31G* program. a, b, and c devices were fabricated based on a published procedure.24 First, a 400–500 nm silicon dioxide layer was thermally grown onto highly doped n-type silicon (100) substrates as gate dielectric. Subsequently, these substrates were cleaned by H2SO4 and H2O2 mixture (7:3, V/V), and deionized water. Then, a, b, and c nanowire fibers were transferred to Si-SiO2 substrates as sensing materials. Finally, electrodes for electrical current determination were made by vapor-depositing Au (4–5 × 10–5 Torr, 0.5 Å/s, 40–60 nm) onto nanowire/fiber with a mask having a channel width of 0.1–0.5 µm. Determination of electrical

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current (I) – time (t) curves was performed at room temperature on a Keithley 4200-SCS system in a test chamber.

RESULTS AND DISCUSSION To reveal how the aggregated process influences chirality, solution-sated characteristics should be a primary consideration. UV-vis spectra of all PDIs in THF (a good solvent, 0.05 mg mL–1) showed three absorption peaks ranging from 400 nm to 600 nm (Figure 1a). This is typical spectra of single perylene molecules in solutions.29 Furthermore, no aggregation-induced Cotton effect was observed in CD spectra (Figure 1b), which is well coincident with their absorption spectra in THF. However, THF/H2O solution at a volume ratio of 1:9 containing compound a and b showed remarkable bisignate CD signals. Figure 1d revealed a well-resolved negative/positive Cotton peaks for compound a at 525 and 600 nm. This bisignate negative/positive Cotton peaks with increasing wavelength indicated that compound a adopted right-handed helical arrangement during aggregated process.25 By contrast, compound b exhibited a positive/negative Cotton peaks at 520 and 600 nm, suggesting its left-handed helical arrangement in THF/H2O solution.25 Different from a and b, c did not show significant Cotton effect in CD spectrum, implying the absence of helical

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aggregation in THF/H2O solution. CD results indicated molecular chirality of sugar subunits can induce supramolecular chirality of perylene molecule in THF/H2O solution, ultimately result in the formation of helical nanowire/fibers (see the discussion below). A remarkable difference was also observed in absorption spectra in THF/H2O. a, b, and c in THF/H2O solutions exhibited red-shifts measuring 11, 17, and 22 nm, respectively, in UV-vis spectra ( Figure 1c), indicating occurrence of π-π stacking.29 This shift implies a head-to-tail configuration in their aggregations that is characteristic as J-type aggregates.30 Results were supported by fluorescent spectra. As shown in Figure S1, a, b, and c in THF/H2O solutions exhibited remarkable red-shifts in fluorescent spectra spanning 65, 58, and 52 nm, respectively, compared with that in THF alone. Strong π-π stacking highly benefits efficient transport of electron and may lead to a significant increase in electrical current (see the discussion below). SEM and TEM were performed to examine aggregation morphologies of a, b, and c in THF/H2O (0.05 mg mL–1). On one hand, right-handed helical wires with diameters of ca. 50–100 nm were generated for a, as shown in Figures 2a and 2d. On the other hand, left-handed helical nanofibers with increased diameters (ca. 100–300 nm) were obtained for b (Figure 2b, 2e). Compared with a and b, only the nanofibers with diameters of ca.

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200–400 nm showed for non-chiral c in their SEM and TEM images (Figure 2c, 2f). Significant difference in morphologies of nanowire/fibers indicated that stereoisomerism of sugar significantly affected aggregation morphologies, and this observation well agrees with our CD results. As a class of electron-deficient organic semiconductor, PDIs show high sensitivity to electron-donor molecules, such as hydrazine. When PDIs were exposed to hydrazine vapor, redox reaction occurred between PDIs and hydrazine molecules, and electrons migrated from hydrazine to PDIs (Figure S2). Then, generated electrons transported along the direction of π-π overlap and ultimately led to changes in electrical current.31, 32 Therefore, electrical currents of a, b, and c in hydrazine gas were investigated using two-probe method, and results revealed high sensitivity of these PDI materials to hydrazine. As displayed in Figure 3, magnitudes of a, b, and c reached ca. 326, 239, and 75 nA in hydrazine vapor (5 ppm), respectively. Sugar-substituted a and b were more sensitive to hydrazine gas, with values ca. 4.4 and 3.2 times higher than that of c. These results indicated that sugar-substituted PDIs show better electrical performance under hydrazine vapor; our previous works were further supported by other chiral PDIs reported by

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Würthner et al.10,

15, 24

With regard to a and b, α-D-glucopyranoside-substituted a

performed better; increase in its electrical current was ca. 1.4 times that of β-D-glucopyranoside-substituted b. Comparing molecular structures of a and b, only the stereoisomerism of sugars changed, implying the remarkable impact of stereoisomerism of sugar on electrical changes. π-π overlaps between adjacent perylene molecules strongly influence the charge carrier mobility in solid-state materials, whereas π-π overlaps are closely related to planarity of perylene skeleton.4 Perfect planarity of perylene skeletons contributes to the formation of

cofacial π-π stacking and provides highly efficient channels for carrier

transport. To further reveal the influence of substituted groups on current changes, torsion angles between the two naphthalene planes in perylene skeleton were studied by virtue of DFT/B3LYP program because such type of angle can remarkably change π-π overlaps. Results showed that compound a had the smallest torsion angle (e.g., C1C2C3C4 dihedral angel, Figure 4) of 30.08°. In the case of b and c, torsion angles of 31.12o and 32.28o were measured, suggesting stronger repulsive effect of bay-substituted groups on twisting of perylene core. We subsequently studied the torsion angle between naphthalene plane and adjacent benzene ring at imide positions. Figure 4 shows torsion

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angles measuring 71.64o and 75.28o for a, 74.20o and 78.78o for b, and 75.20o and 89.20o for c.33 Differential torsion angle between naphthalene plane and adjacent benzene ring for a, b, and c induced variation in torsion angle of two naphthalene mean-square planes. Subsequently, we investigated dimer structure of observed materials using the semi-empirical method (AM1). As shown in Figure S4, when molecules are coaxially arranged, compared with c (a shift of ~12.8 Å), smaller torsion angle caused shifts of ~11.1 Å for α-D-glucopyranoside substituted a and ~11.4 Å for β-D-glucopyranoside substituted b along the long axis of molecules. As larger π-π overlaps contribute to high efficient migrating of charge carrier, larger torsion angles and shifts long axis would reduce π-π overlaps between adjacent perylene skeletons and further decreased carrier mobility, thus resulting in smaller increasing in current for c device. To delineate differences in their current changes, crystal phases of a, b, and c nanostructures were further studied by XRD determination (Figure 5). XRD profiles showed that for a, b, and c, long axes of unit cells measured 20.40, 20.18, and 20.21 Å (2θ = 4.33°, 4.38° and 3.36°), respectively, which were shorter than the total length of corresponding PDIs of 28.58, 28.58, and 22.89 Å (along the long axis of PDIs; after DFT calculation; B3LYP/6-31G*). Compared with that of c, unit cell of a and b more

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significantly shortened along the longitudinal direction, implying strong hydrogen interaction between adjacent carbohydrate groups. This strong hydrogen interaction also induced enhancement of π-π stacking between adjacent perylene cores. Figure 5 shows a diffraction peak at ca. 2θ = 26.66° and 26.31° (interplanar spacing of 3.35 Å and 3.39 Å) for a and b, respectively, suggesting that strong π-π stacking existed in samples.4 Data were further supported by calculation results. Vertical distance between adjacent perylene skeletons of a, b, and c measured 3.36, 3.38, and 3.46 Å (Figure S3), respectively; these values coincide well with our XRD results. As interplanar spacing is closely associated with efficient transport of carriers, we speculated that smaller π-π stacking spacing of compound a may significantly improve its electrical performance compared with that of b. Using the presented data, detailed analyses were conducted to determine differences in increased currents of a, b, and c according to the following arguments. Compared to compound a and b, c showed the poorest electrical performance in hydrazine vapor. This finding was possibly caused by a larger shift along the long axis (12.8 Å) and largest torsion angle (32.28o). These effects reduced π-π overlaps between adjoining perylene skeletons and reduced carrier mobility, resulting in the smallest increase in electrical

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currents. In hydrazine vapor, more remarkable improvement in current was observed for a devices compared with that of b. A smaller torsion angle of 30.08o led to a larger π-π overlap between neighboring a, thus enhancing carrier mobility. On the other hand, a smaller π-π interplanar spacing of 3.35 Å made the migrating of carrier transport high efficient. These findings led to more remarkable improvement in electrical current for a device.

CONCLUSIONS In

conclusion,

modulated

intermolecular

interactions

through

modified

stereoisomerism of sugar groups can induce formation of right-handed and left-handed helical nanowire fibers for α-D-glucopyranoside and β-D-glucopyranoside-substituted PDIs, respectively, in THF/H2O solution. These intermolecular interactions influenced π-π overlap and π-π spacing in materials, and showed in change of electrical current. Determination

of

electrical

current

in

hydrazine

vapor

revealed

that

both

sugar-substituted PDIs exhibited more enhanced current change relative to their achiral counterparts as a result of larger π-π orbital overlap between adjacent perylene cores. A larger π-π orbital overlap and a smaller π-π interplanar spacing caused more remarkable improvement in electrical current of α-D-glucopyranoside-substituted PDIs than that of

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β-D-glucopyranoside-substituted PDIs. This study provides an elaborated route for modulating helical aggregations and optoelectrical properties through stereoisomerism of chiral groups.

SUPPORTING INFORMATION Synthesis and characterization of a, b, and c; energetically preferable geometry of a, b, and c monomers and dimers; fluorescence spectra and schemes for devices.

ACKNOWLEDGMENTS The study was supported by the National Natural Science Foundation of China (No: 21572045), the Natural Science Foundation of Henan Province (No: 162300410017), the program for Science & Technology Innovation Talents in the Universities of Henan Province (No: 16HASTIT008 and No: 2013GGJS237), and Henan University (No: Y1516019 and Y1516040). a.

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(31) Huang, Y.; Wang, J.; Fu, L.; Kuang, W.; Shi, J. Effect of Core-Substituted Groups on Sensing Properties Based on Single Micro/Nanorod of Perylenediimide Derivatives. Sens. Actuators. B 2013, 188, 411–416. (32) Che, Y.; Datar, A.; Yang, X.; Naddo, T.; Zhao, J.; Zang, L. Enhancing One-Dimensional

Charge Transport Through Intermolecular π-Electron Delocalization: Conductivity Improvement for Organic Nanobelts. J. Am. Chem. Soc. 2007, 129, 6354–6355. (33) The authors proposed the torsion angle may result from repulsive interaction between the N-substituted benzene ring and carbonyl oxygen atom (marked by blue circle in Figure S4). Concerning the difference in torsion angle for a, b and c, the authors considered the behavior may root in the difference in Van der Waals' force between oxygen and hydrogen atom (marked by green circle in Figure S4). A special Van der Waals' force between oxygen and hydrogen atom for a and b made the repulsive interaction weaken and leaded to smaller torsion angle. Whereas c possesses the largest torsion angle due to the lack of the special Van der Waals' force (Figure S4). Because the Van der Waals' force is related to distance between oxygen and hydrogen atom, the Van der Waals' force may change with variation of position of oxygen and hydrogen atom, and thus lead to the differential torsion angle for a and b, although both of them have the same substituted groups at the imide N position.

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Figure and Scheme Captions

Scheme 1. Chemical structure of compound a, b and c. Figure 1. UV-vis and CD spectra in (a, b) THF and (c, d) THF/H2O (1:9, V/V, 0.05 mg mL-1) for compound a, b and c. Figure 2. SEM and TEM images for compound (a, d) a, (b, e) b and (c, f) c nanofibers obtained from THF/H2O (1:9, V/V, 0.05 mg mL-1). Figure 3. Current modulation (I) -time (t) curves of compound a, b and c devices in hydrazine. Figure 4. Torsion angle between the two naphthalene planes of perylene core (i.e., C1C2C3C4 dihedral angel) for compound a (30.08o), b (31.12o) and c (32.28o), and the torsion angle between naphthalene and adjacent benzene ring. Figure 5. X-ray diffraction patterns with d spacing given (Å) of a, b and c nanowire(fiber).

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Scheme 1.

Figure 1.

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Figure 2.

Figure 3.

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Figure 4.

Figure 5.

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Table of Contents

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Tunable Supramolecular Helical Aggregate and ... - ACS Publications

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