Chiral Pentaphenylpyrrole Derivatives with Aggregation-Induced Emission Enhancement and Aggregation Induced Circular Dichroism and Their Helical Self-assembly
A pair of enantiomers (S)-P5PdiAM and (R)-P5PdiAM containing two chiral substituents, and their raceme rac-P5PdiAM were synthesized by introducing (R)-/(S)- or racemic 1-phenylethylamine into 1-biphenyl-2,3,4,5-tetraphenylpyrrole. The target compounds all show weak aggregation-induced emission enhan...
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EDP Sciences
2021-01-01
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doaj-d92bdb6c16c94f9b9793db40517bf8f62021-06-11T07:21:12ZengEDP SciencesE3S Web of Conferences2267-12422021-01-012670201210.1051/e3sconf/202126702012e3sconf_icsce2021_02012Chiral Pentaphenylpyrrole Derivatives with Aggregation-Induced Emission Enhancement and Aggregation Induced Circular Dichroism and Their Helical Self-assemblyWang Yuanyuan0Zhang Longlong1Zhi Junge2School of Chemistry and Chemical Engineering, Beijing Key Laboratory of Photoelectronic/Electrophotonic Conversion Materials, Beijing Institute of TechnologySchool of Chemistry and Chemical Engineering, Beijing Key Laboratory of Photoelectronic/Electrophotonic Conversion Materials, Beijing Institute of TechnologySchool of Chemistry and Chemical Engineering, Beijing Key Laboratory of Photoelectronic/Electrophotonic Conversion Materials, Beijing Institute of TechnologyA pair of enantiomers (S)-P5PdiAM and (R)-P5PdiAM containing two chiral substituents, and their raceme rac-P5PdiAM were synthesized by introducing (R)-/(S)- or racemic 1-phenylethylamine into 1-biphenyl-2,3,4,5-tetraphenylpyrrole. The target compounds all show weak aggregation-induced emission enhancement (AIEE) characteristics in the DMSO/H2O mixed system, indicating that the introduction of chirality hardly affect the photophysical properties of the compound. In addition, the chiral compounds (S)-P5PdiAM and (R)-P5PdiAM show strong circular dichroism (CD) signals in THF/H2O mixed solution with a water fraction of 70%, that is, they exhibit aggregation-induced circular dichroism characteristics (AICD). Because the aggregates of (S)-P5PdiAM and (R)-P5PdiAM emit weakly, there is no circularly polarized luminescence (CPL) signals upon aggregation. The chiral compounds (S)-P5PdiAM and (R)-P5PdiAM can self-assemble to form helical nanofibers in a THF/H2O mixture with a water fraction of 70%, while the racemic rac-P5PdiAM assembled to form nano-particles, indicating that chiral substituents have a great influence on the self-assembly and the morphologies of the nano-aggregates.https://www.e3s-conferences.org/articles/e3sconf/pdf/2021/43/e3sconf_icsce2021_02012.pdf |
collection |
DOAJ |
language |
English |
format |
Article |
sources |
DOAJ |
author |
Wang Yuanyuan Zhang Longlong Zhi Junge |
spellingShingle |
Wang Yuanyuan Zhang Longlong Zhi Junge Chiral Pentaphenylpyrrole Derivatives with Aggregation-Induced Emission Enhancement and Aggregation Induced Circular Dichroism and Their Helical Self-assembly E3S Web of Conferences |
author_facet |
Wang Yuanyuan Zhang Longlong Zhi Junge |
author_sort |
Wang Yuanyuan |
title |
Chiral Pentaphenylpyrrole Derivatives with Aggregation-Induced Emission Enhancement and Aggregation Induced Circular Dichroism and Their Helical Self-assembly |
title_short |
Chiral Pentaphenylpyrrole Derivatives with Aggregation-Induced Emission Enhancement and Aggregation Induced Circular Dichroism and Their Helical Self-assembly |
title_full |
Chiral Pentaphenylpyrrole Derivatives with Aggregation-Induced Emission Enhancement and Aggregation Induced Circular Dichroism and Their Helical Self-assembly |
title_fullStr |
Chiral Pentaphenylpyrrole Derivatives with Aggregation-Induced Emission Enhancement and Aggregation Induced Circular Dichroism and Their Helical Self-assembly |
title_full_unstemmed |
Chiral Pentaphenylpyrrole Derivatives with Aggregation-Induced Emission Enhancement and Aggregation Induced Circular Dichroism and Their Helical Self-assembly |
title_sort |
chiral pentaphenylpyrrole derivatives with aggregation-induced emission enhancement and aggregation induced circular dichroism and their helical self-assembly |
publisher |
EDP Sciences |
series |
E3S Web of Conferences |
issn |
2267-1242 |
publishDate |
2021-01-01 |
description |
A pair of enantiomers (S)-P5PdiAM and (R)-P5PdiAM containing two chiral substituents, and their raceme rac-P5PdiAM were synthesized by introducing (R)-/(S)- or racemic 1-phenylethylamine into 1-biphenyl-2,3,4,5-tetraphenylpyrrole. The target compounds all show weak aggregation-induced emission enhancement (AIEE) characteristics in the DMSO/H2O mixed system, indicating that the introduction of chirality hardly affect the photophysical properties of the compound. In addition, the chiral compounds (S)-P5PdiAM and (R)-P5PdiAM show strong circular dichroism (CD) signals in THF/H2O mixed solution with a water fraction of 70%, that is, they exhibit aggregation-induced circular dichroism characteristics (AICD). Because the aggregates of (S)-P5PdiAM and (R)-P5PdiAM emit weakly, there is no circularly polarized luminescence (CPL) signals upon aggregation. The chiral compounds (S)-P5PdiAM and (R)-P5PdiAM can self-assemble to form helical nanofibers in a THF/H2O mixture with a water fraction of 70%, while the racemic rac-P5PdiAM assembled to form nano-particles, indicating that chiral substituents have a great influence on the self-assembly and the morphologies of the nano-aggregates. |
url |
https://www.e3s-conferences.org/articles/e3sconf/pdf/2021/43/e3sconf_icsce2021_02012.pdf |
work_keys_str_mv |
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