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Rational design of small indolic squaraine dyes with large two-photon absorption cross section
Small organic dyes with large two-photon absorption (TPA) cross sections (δ) are more desirable in many applications compared with large molecules. Herein, we proposed a facile theoretical method for the fast screening of small organic molecules as potential TPA dyes. This method is based on a theor...
Autores principales: | , , , , , , , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
Royal Society of Chemistry
2015
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5590541/ https://www.ncbi.nlm.nih.gov/pubmed/28936317 http://dx.doi.org/10.1039/c4sc02165g |
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author | Sun, Chun-Lin Liao, Qing Li, Ting Li, Jun Jiang, Jian-Qiao Xu, Zhen-Zhen Wang, Xue-Dong Shen, Rong Bai, De-Cheng Wang, Qiang Zhang, Sheng-Xiang Fu, Hong-Bing Zhang, Hao-Li |
author_facet | Sun, Chun-Lin Liao, Qing Li, Ting Li, Jun Jiang, Jian-Qiao Xu, Zhen-Zhen Wang, Xue-Dong Shen, Rong Bai, De-Cheng Wang, Qiang Zhang, Sheng-Xiang Fu, Hong-Bing Zhang, Hao-Li |
author_sort | Sun, Chun-Lin |
collection | PubMed |
description | Small organic dyes with large two-photon absorption (TPA) cross sections (δ) are more desirable in many applications compared with large molecules. Herein, we proposed a facile theoretical method for the fast screening of small organic molecules as potential TPA dyes. This method is based on a theoretical analysis to the natural transition orbitals (NTOs) directly associated with the TPA transition. Experimental results on the small indolic squaraine dyes (ISD) confirmed that their TPA cross sections is strongly correlated to the delocalization degree of the NTOs of the S(2) excited states. Aided by this simple and intuitive method, we have successfully designed and synthesized a small indolic squaraine dye (ISD) with a remarkable δ value above 8000 GM at 780 nm. The ISD dye also exhibits a high singlet oxygen generation quantum yield about 0.90. The rationally designed TPA dye was successfully applied in both two-photon excited fluorescence cell imaging and in vivo cerebrovascular blood fluid tracing. |
format | Online Article Text |
id | pubmed-5590541 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2015 |
publisher | Royal Society of Chemistry |
record_format | MEDLINE/PubMed |
spelling | pubmed-55905412017-09-21 Rational design of small indolic squaraine dyes with large two-photon absorption cross section Sun, Chun-Lin Liao, Qing Li, Ting Li, Jun Jiang, Jian-Qiao Xu, Zhen-Zhen Wang, Xue-Dong Shen, Rong Bai, De-Cheng Wang, Qiang Zhang, Sheng-Xiang Fu, Hong-Bing Zhang, Hao-Li Chem Sci Chemistry Small organic dyes with large two-photon absorption (TPA) cross sections (δ) are more desirable in many applications compared with large molecules. Herein, we proposed a facile theoretical method for the fast screening of small organic molecules as potential TPA dyes. This method is based on a theoretical analysis to the natural transition orbitals (NTOs) directly associated with the TPA transition. Experimental results on the small indolic squaraine dyes (ISD) confirmed that their TPA cross sections is strongly correlated to the delocalization degree of the NTOs of the S(2) excited states. Aided by this simple and intuitive method, we have successfully designed and synthesized a small indolic squaraine dye (ISD) with a remarkable δ value above 8000 GM at 780 nm. The ISD dye also exhibits a high singlet oxygen generation quantum yield about 0.90. The rationally designed TPA dye was successfully applied in both two-photon excited fluorescence cell imaging and in vivo cerebrovascular blood fluid tracing. Royal Society of Chemistry 2015-01-01 2014-10-07 /pmc/articles/PMC5590541/ /pubmed/28936317 http://dx.doi.org/10.1039/c4sc02165g Text en This journal is © The Royal Society of Chemistry 2014 http://creativecommons.org/licenses/by/3.0/ This is an Open Access article distributed under the terms of the Creative Commons Attribution 3.0 Unported License (http://creativecommons.org/licenses/by/3.0/) which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. |
spellingShingle | Chemistry Sun, Chun-Lin Liao, Qing Li, Ting Li, Jun Jiang, Jian-Qiao Xu, Zhen-Zhen Wang, Xue-Dong Shen, Rong Bai, De-Cheng Wang, Qiang Zhang, Sheng-Xiang Fu, Hong-Bing Zhang, Hao-Li Rational design of small indolic squaraine dyes with large two-photon absorption cross section |
title | Rational design of small indolic squaraine dyes with large two-photon absorption cross section
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title_full | Rational design of small indolic squaraine dyes with large two-photon absorption cross section
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title_fullStr | Rational design of small indolic squaraine dyes with large two-photon absorption cross section
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title_full_unstemmed | Rational design of small indolic squaraine dyes with large two-photon absorption cross section
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title_short | Rational design of small indolic squaraine dyes with large two-photon absorption cross section
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title_sort | rational design of small indolic squaraine dyes with large two-photon absorption cross section |
topic | Chemistry |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5590541/ https://www.ncbi.nlm.nih.gov/pubmed/28936317 http://dx.doi.org/10.1039/c4sc02165g |
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