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Integration of inherent and induced chirality into subphthalocyanine analogue

Conventional conjugated systems are characteristic of only either inherent or induced chirality because of synthetic challenge in combination of chiral segment into the main chromophore. In this work, chiral binaphthyl segment is directly fused into the central chromophore of a subphthalocyanine ske...

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Autores principales: Zhao, Luyang, Qi, Dongdong, Wang, Kang, Wang, Tianyu, Han, Bing, Tang, Zhiyong, Jiang, Jianzhuang
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Nature Publishing Group 2016
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4904797/
https://www.ncbi.nlm.nih.gov/pubmed/27294871
http://dx.doi.org/10.1038/srep28026
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author Zhao, Luyang
Qi, Dongdong
Wang, Kang
Wang, Tianyu
Han, Bing
Tang, Zhiyong
Jiang, Jianzhuang
author_facet Zhao, Luyang
Qi, Dongdong
Wang, Kang
Wang, Tianyu
Han, Bing
Tang, Zhiyong
Jiang, Jianzhuang
author_sort Zhao, Luyang
collection PubMed
description Conventional conjugated systems are characteristic of only either inherent or induced chirality because of synthetic challenge in combination of chiral segment into the main chromophore. In this work, chiral binaphthyl segment is directly fused into the central chromophore of a subphthalocyanine skeleton, resulting in a novel type of chiral subphthalocyanine analogue (R/S)-1 of integrated inherent and induced chirality. Impressively, an obviously enhanced optical activity is discerned for (R/S)-1 molecules, and corresponding enhancement mechanism is elucidated in detail. The synthesis strategy based on rational molecular design will open the door towards fabrication of chiral materials with giant optical activity, which will have great potential in chiroptical devices.
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spelling pubmed-49047972016-06-14 Integration of inherent and induced chirality into subphthalocyanine analogue Zhao, Luyang Qi, Dongdong Wang, Kang Wang, Tianyu Han, Bing Tang, Zhiyong Jiang, Jianzhuang Sci Rep Article Conventional conjugated systems are characteristic of only either inherent or induced chirality because of synthetic challenge in combination of chiral segment into the main chromophore. In this work, chiral binaphthyl segment is directly fused into the central chromophore of a subphthalocyanine skeleton, resulting in a novel type of chiral subphthalocyanine analogue (R/S)-1 of integrated inherent and induced chirality. Impressively, an obviously enhanced optical activity is discerned for (R/S)-1 molecules, and corresponding enhancement mechanism is elucidated in detail. The synthesis strategy based on rational molecular design will open the door towards fabrication of chiral materials with giant optical activity, which will have great potential in chiroptical devices. Nature Publishing Group 2016-06-13 /pmc/articles/PMC4904797/ /pubmed/27294871 http://dx.doi.org/10.1038/srep28026 Text en Copyright © 2016, Macmillan Publishers Limited http://creativecommons.org/licenses/by/4.0/ This work is licensed under a Creative Commons Attribution 4.0 International License. The images or other third party material in this article are included in the article’s Creative Commons license, unless indicated otherwise in the credit line; if the material is not included under the Creative Commons license, users will need to obtain permission from the license holder to reproduce the material. To view a copy of this license, visit http://creativecommons.org/licenses/by/4.0/
spellingShingle Article
Zhao, Luyang
Qi, Dongdong
Wang, Kang
Wang, Tianyu
Han, Bing
Tang, Zhiyong
Jiang, Jianzhuang
Integration of inherent and induced chirality into subphthalocyanine analogue
title Integration of inherent and induced chirality into subphthalocyanine analogue
title_full Integration of inherent and induced chirality into subphthalocyanine analogue
title_fullStr Integration of inherent and induced chirality into subphthalocyanine analogue
title_full_unstemmed Integration of inherent and induced chirality into subphthalocyanine analogue
title_short Integration of inherent and induced chirality into subphthalocyanine analogue
title_sort integration of inherent and induced chirality into subphthalocyanine analogue
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4904797/
https://www.ncbi.nlm.nih.gov/pubmed/27294871
http://dx.doi.org/10.1038/srep28026
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