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Two-photon-absorption properties of pyrene-based dipolar D-π-A fluorophores

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journal contribution
posted on 05.10.2018, 09:58 by Chuan-Zeng Wang, Ruoyao Zhang, Koya Sakaguchi, Xing Feng, Xiaoqiang Yu, Mark Elsegood, Simon J. Teat, Carl Redshaw, Takehiko Yamato
Two‐photon absorption (TPA) properties of pyrene‐based derivatives are rare as a result of the limited number of controllable synthetic methods to prepare them. However, these materials are in great demand given their potential practical application in photics and biological imaging. Herein, we present a set of pyrene‐based dipolar donor‐π‐acceptor (D‐π‐A) fluorophores with a wide‐range of color tuning and large TPA cross‐sections (up to 2200 GM at 780 nm) by regioselective substitution at the 1,3‐ and 6,8‐positions under the perspective of theoretical analysis. The linear and nonlinear optical properties of these compounds have been studied. The near‐identical emission wavelengths between the two‐photon‐excited fluorescence (TPEF) and one‐photon excited fluorescence (OPEF) indicated that they are generated from the same fluorescent excited state by either one‐ or two‐photon excitation. With the exception of the strong donor [N(CH3)2] appended fluorophore, the TPEF exhibited a large red‐shift compared with the OPEF spectra as a result of the complicated working mechanisms in operation, including intramolecular charge transfer (ICT) and twisted intramolecular charge transfer (TICT). All fluorophores exhibit high two‐photon cross‐sections (or two‐photon brightness, δΦ), especially for 1348 GM, which indicated that these materials can be used as colorants for probe and bioimaging applications.

Funding

This present work was performed under the Cooperative Research Program of “Network Joint Research Center for Materials and Devices (Institute for Materials Chemistry and Engineering, Kyushu University)"

History

School

  • Science

Department

  • Chemistry

Published in

ChemPhotoChem

Volume

2

Pages

749 - 756 (8)

Citation

WANG, C-Z. ... et al., 2018. Two-photon-absorption properties of pyrene-based dipolar D-π-A fluorophores. ChemPhotoChem, 2, pp. 749-756.

Publisher

© Wiley-VCH

Version

AM (Accepted Manuscript)

Publisher statement

This work is made available according to the conditions of the Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International (CC BY-NC-ND 4.0) licence. Full details of this licence are available at: https://creativecommons.org/licenses/by-nc-nd/4.0/

Acceptance date

15/04/2018

Publication date

2018-04-15

Notes

This is the pre-peer reviewed version of the following article: WANG, C-Z. ... et al., 2018. Two-photon-absorption properties of pyrene-based dipolar D-π-A fluorophores. ChemPhotoChem, 2, pp. 749-756, which has been published in final form at https://doi.org/10.1002/cptc.201800053. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Use of Self-Archived Versions.

ISSN

2367-0932

Language

en

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