Tuning the supramolecular chirality and optoelectronic performance of chiral perylene diimide nanowires <i>via N</i>-substituted side chain engineering

Shang, Xiaobo; Song, Inho; Lee, Ju Han; Han, Myeonggeun; Kim, Jin Chul; Ohtsu, Hiroyoshi; Ahn, Jaeyong; Kwak, Sang Kyu; Oh, Joon Hak

doi:10.1039/c9tc01597c

Cited by 24 publications

(23 citation statements)

References 44 publications

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“…Intrigued by our earlier findings on one-dimensional (1D) supramolecular nanomaterials for a series of N,N′-substituted chiral PDIs, 3,11,12 and given the urgency of the need in the aforementioned fields, we explored the possibility of fabricating 2D supramolecular chiral assemblies by rationally tuning the bay substitution at the PDIs and thus synthesized coretetrachlorinated chiral PDIs, i.e., 5,6,12,13-tetrachloro-2,9- and triangle/hexagon (ClCPDI-Ph-DMF) morphologies, respectively. In addition, their circular dichroism (CD) signals were also quite different, indicating that the solvent had a major impact on the self-assembly and supramolecular chirality of chiral OSCs.…”

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confidence: 87%

“…8,10 In our previous work, we T also discovered that chirality in the ordered supramolecular nanostructures can be increased through both intramolecular and intermolecular interactions of perylene diimides (PDIs). 3,11,12 Based on their relevance to physics, chemistry, biology, and materials science, 13 chiral supramolecules are good candidates for applications in various fields, including chiral recognition, catalysis, sensing, and optical devices. 3,9,12 Two-dimensional (2D) organic photoactive crystals, which combine the inherent advantages of organic photoactive layers with a 2D structural platform, are highly suitable for use in next-generation organic field-effect transistors (OFETs) with optoelectronic functions and enhanced charge transport, due to their morphological features, low-cost fabrication, light weight, and molecular diversity.…”

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confidence: 99%

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Surface-Doped Quasi-2D Chiral Organic Single Crystals for Chiroptical Sensing

et al. 2020

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Chiral organic optoelectronics using circularly polarized light (CPL) as the key element in the photonic signal has recently emerged as a next-generation photonic technology. However, it remains challenging to simultaneously achieve high polarization selectivity and superior optoelectronic performance. Supramolecular two-dimensional (2D) chiral organic single crystals may be good candidates for this purpose due to their defect-free nature, molecular diversity, and morphologies. Here, quasi-2D single crystals of chiral perylene diimides with parallelogram and triangle/hexagon morphologies have been selectively fabricated via self-assembly using different cosolvent systems. These materials exhibit amplified circular dichroism (CD) spectral signals, due to their molecular packing modes and supramolecular chirality. Through molecular surface n-doping using hydrazine, chiral single crystals exhibit electron mobility surpassing 1.0 cm 2 V −1 s −1 , which is one of the highest among chiral organic semiconductors, and excellent optoelectronic functions. Theoretical calculations reveal that the radical anions formed by n-doping increase the electron affinity and/or reduce the energy gap, thus facilitating electron transport. More importantly, the doped organic chiral crystals selectively discriminate CPL handedness with a high anisotropy factor of photoresponsivity (∼0.12). These results demonstrate that surface-doped quasi-2D chiral organic single crystals are highly promising for chiral optoelectronics.

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Surface-Doped Quasi-2D Chiral Organic Single Crystals for Chiroptical Sensing

et al. 2020

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“…To our knowledge, there have been few investigations regarding the OPTs of self‐assembled supramolecules with the “majority‐rules” principle. Based on our previous researches on chiral supramolecules of perylene diimides (PDIs) and their applications in OPTs, [ 18–20 ] we subsequently investigated the “majority‐rules” effect on the supramolecular chirality and optoelectronic performance of PDIs. Chiral tetrachloro‐substituted perylene diimides (ClCPDI‐Ph) with different ee values, such as 100% and 0%, were self‐assembled into quasi‐2D crystals and 1D NWs, respectively.…”

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confidence: 99%

“Majority‐Rules” Effect on Supramolecular Chirality and Optoelectronic Properties of Chiral Tetrachloro‐Perylene Diimides

Shang

Song

Han

et al. 2020

Advanced Optical Materials

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Supramolecular chirality has attracted a great deal of attention as a platform for both fundamental study and chirality amplification in various research fields. Compared with the “sergeants‐and‐soldiers” principle, the “majority‐rules” principle, which affects chirality amplification in supramolecular systems, is rarely reported for nano/microstructures. Here, chiral tetrachloro‐substituted perylene diimides are synthesized that self‐assemble into chiral supramolecules with different degrees of enantiomeric excess (ee). Interestingly, it is found that quasi‐2D crystals are gradually transferred to 1D nanowires (NWs) with ee from 100% to 0%. In the racemic system, chiral self‐discrimination is observed due to the greater thermodynamic stability of heterochiral crystals than the homochiral counterparts, judging from the theoretical studies. Circular dichroism analysis indicates that the self‐assembled system with different ee values shows different peaks due to their unique molecular ordering for supramolecular exciton coupling. On measurement in optoelectronic devices, racemic 1D NWs show better charge transport ability than enantiomeric quasi‐2D crystals. These results provide guidelines for tuning the supramolecular chirality and optoelectronic performance of self‐assembled systems via the “majority‐rules” principle.

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“…We present here the symmetric PBI with D-phenylalanine in the amide position which acts as a chiral sensor only for the D form of the phenylalanine. According to our knowledge this type of recognition can pave the road in the direction of chiral discrimination (Avinash and Govindaraju, 2012;Sato et al, 2019;Shang et al, 2019).…”

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confidence: 98%

Supramolecular Chiral Discrimination of D-Phenylalanine Amino Acid Based on a Perylene Bisimide Derivative

Bettini

Syrgiannis

Ottolini

et al. 2020

Front. Bioeng. Biotechnol.

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The interaction between homochiral substituted perylene bisimide (PBI) molecule and the D enantiomer of phenylalanine amino acid was monitored. Spectroscopic transitions of PBI derivative in aqueous solution in the visible range were used to evaluate the presence of D-phenylalanine. UV-visible, fluorescence, FT-IR, and AFM characterizations showed that D-phenylalanine induces significant variations in the chiral perylene derivative aggregation state and the mechanism is enantioselective as a consequence of the 3D analyte structure. The interaction mechanism was further investigated in presence of interfering amino acid (D-serine and D-histidine) confirming that both chemical structure and its 3D structure play a crucial role for the amino acid discrimination. A D-phenylalanine fluorescence sensor based on perylene was proposed. A limit of detection (LOD) of 64.2 ± 0.38 nM was calculated in the range 10 −7 -10 −5 M and of 1.53 ± 0.89 µM was obtained in the range 10 −5 and 10 −3 M.

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Tuning the supramolecular chirality and optoelectronic performance of chiral perylene diimide nanowires via N-substituted side chain engineering

Abstract: An efficient method using N-substituted side chain engineering is demonstrated for tuning the supramolecular chirality and optoelectronics of perylene diimides.

Cited by 24 publications

References 44 publications

Surface-Doped Quasi-2D Chiral Organic Single Crystals for Chiroptical Sensing

Surface-Doped Quasi-2D Chiral Organic Single Crystals for Chiroptical Sensing

“Majority‐Rules” Effect on Supramolecular Chirality and Optoelectronic Properties of Chiral Tetrachloro‐Perylene Diimides

Supramolecular Chiral Discrimination of D-Phenylalanine Amino Acid Based on a Perylene Bisimide Derivative

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