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

Wang, Chuan Zeng; Zhang, Ruoyao; Sakaguchi, Koya; Feng, Xing; Yu, Xiaoqiang; Elsegood, Mark R. J.; Teat, Simon J.; Redshaw, Carl; Yamato, Takehiko

Abstract

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.

Citation

Wang, C. Z., Zhang, R., Sakaguchi, K., Feng, X., Yu, X., Elsegood, M. R. J., …Yamato, T. (2018). Two-photon-absorption properties of pyrene-based dipolar D-π-A fluorophores. Chemphotochem, 2(8), 749-756. https://doi.org/10.1002/cptc.201800053

• Journal Article Type: Article
• Acceptance Date: Apr 9, 2018
• Online Publication Date: Apr 15, 2018
• Publication Date: Aug 14, 2018
• Deposit Date: May 24, 2018
• Publicly Available Date: Apr 16, 2019
• Journal: ChemPhotoChem
• Print ISSN: 2367-0932
• Electronic ISSN: 2367-0932
• Peer Reviewed: Peer Reviewed
• Volume: 2
• Issue: 8
• Pages: 749-756
• DOI: https://doi.org/10.1002/cptc.201800053
• Keywords: Charge transfer; Dipolar molecules; Donor–acceptor systems; Pyrene; Two-photon absorption
• Public URL: https://hull-repository.worktribe.com/output/848236
• Publisher URL: https://onlinelibrary.wiley.com/doi/abs/10.1002/cptc.201800053
• Additional Information: This is the peer reviewed version of the following article: Wang, C. , Zhang, R. , Sakaguchi, K. , Feng, X. , Yu, X. , Elsegood, M. R., Teat, S. J., Redshaw, C. and Yamato, T. (2018), Two‐Photon‐Absorption Properties of Pyrene‐Based Dipolar D‐π‐A Fluorophores. ChemPhotoChem. . doi: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.