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Issue 1, 2015
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Rational design of small indolic squaraine dyes with large two-photon absorption cross section

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Abstract

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 S2 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.

Graphical abstract: Rational design of small indolic squaraine dyes with large two-photon absorption cross section

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Supplementary files

Article information


Submitted
21 Jul 2014
Accepted
07 Oct 2014
First published
07 Oct 2014

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2015,6, 761-769
Article type
Edge Article
Author version available

Rational design of small indolic squaraine dyes with large two-photon absorption cross section

C. Sun, Q. Liao, T. Li, J. Li, J. Jiang, Z. Xu, X. Wang, R. Shen, D. Bai, Q. Wang, S. Zhang, H. Fu and H. Zhang, Chem. Sci., 2015, 6, 761
DOI: 10.1039/C4SC02165G

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