Effect of Differential Self-Assembly on Mechanochromic Luminescence of Fluorene-Benzothiadiazole-Based Fluorophores

Overview

Journal ACS Omega

Publisher American Chemical Society

Specialty Chemistry

Date 2019 Aug 29

PMID 31457431

Citations 2

Authors

Karattu Chali Naeem

Kadaikkara Neenu

Vijayakumar C Nair

Affiliations

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Abstract

Supramolecular self-assembly is an excellent tool for controlling the optical and electronic properties of chromophore-based molecular systems. Herein, we demonstrate how differential self-assembly affects mechanoresponsive luminescence of fluorene-benzothiadiazole-based fluorophores. We have synthesized two donor-acceptor-donor-type conjugated oligomers consisting of fluorene as the donor and benzothiadiazole as the acceptor. For facile self-assembly, both molecules are end-functionalized with hydrogen-bonding amide groups. Differential self-assembly was induced by attaching alkyl chains of different lengths onto the fluorene moiety: hexyl () and dodecyl (). The molecules self-assemble to form well-defined nanostructures in nonpolar solvents and solvent mixtures. Although their optical properties in solution are not affected by the alkyl chain length, significant effects were observed in the self-assembled state, particularly in the excitation energy migration properties. As a result, remarkable differences were observed in the mechanochromic luminescence properties of the molecules. A precise structure-property correlation is made using UV-visible absorption and fluorescence spectroscopy, time-correlated single-photon counting analysis, scanning electron microscopy, and X-ray diffraction spectroscopy.

Citing Articles

High-contrast mechanochromic benzothiadiazole derivatives based on a triphenylamine or a carbazole unit.

Zhu Y, Xia H, Yao L, Huang D, Song J, He H RSC Adv. 2022; 9(13):7176-7180.

PMID: 35519968 PMC: 9061094. DOI: 10.1039/c9ra00141g.

Threonine-Based Stimuli-Responsive Nanoparticles with Aggregation-Induced Emission-Type Fixed Cores for Detection of Amines in Aqueous Solutions.

Kataoka K, Nakabayashi K, Lo C, Mori H Polymers (Basel). 2022; 14(7).

PMID: 35406233 PMC: 9002686. DOI: 10.3390/polym14071362.

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