Issue 33, 2021

Syntheses, structures, and one- and two-photon excited fluorescence of dimesitylboryl-ended quadrupolar hybrid oligothiophenes

Abstract

Four dimesitylboryl-ended quasi-oligothiophene chromophores composed of central 2,1,3-benzothiadiazole (1), thieno[3,2-b]thiophene (2), and benzo[1,2-b:4,5-b′]dithiophene (3, 4), respectively, have been synthesized via concise Pd-catalyzed cross-coupling reactions. The crystal structures of 1–3 and a mono dimesitylboryl-ended derivative (5) were determined. The extensive examination and comparison of their photo-physical properties indicate that the electron-donating or -accepting features of the central moiety may greatly tune their photon absorption and emission properties. Among these quasi-oligothiophene chromophores, 2,1,3-benzothiadiazole derivative 1 has the highest photoluminescence quantum yield (0.70) and longest fluorescence lifetime (12.89 ns). In particular, the excitation spectra of their two-photon excited fluorescence (TPEF) in the range of 740–880 nm demonstrate that the maximum of the two-photon absorption cross-sections of the A–π–D–π–A type compound 4 is nearly 8 times that of A–π–A–π–A type compound 1, which clearly proves that the length of the conjugated bridge and the number of efficient delocalized electrons may play important roles in enhancing the two-photon absorption.

Graphical abstract: Syntheses, structures, and one- and two-photon excited fluorescence of dimesitylboryl-ended quadrupolar hybrid oligothiophenes

Supplementary files

Article information

Article type
Paper
Submitted
10 feb 2021
Accepted
26 mar 2021
First published
30 mar 2021

New J. Chem., 2021,45, 15035-15042

Syntheses, structures, and one- and two-photon excited fluorescence of dimesitylboryl-ended quadrupolar hybrid oligothiophenes

S. Zhou, S. Zhang, J. Li, Z. Liu and X. Yu, New J. Chem., 2021, 45, 15035 DOI: 10.1039/D1NJ00694K

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements