Issue 12, 2023

Fluorophore unit controlled photoswitching of hydrazone derivatives: reversible and irreversible off–on/dual-color fluorescence photoswitches

Abstract

Hydrazone photoswitching functionalities integrated with three different fluorophore units (perylene (PY-PH), tetraphenylethylene (TPE-PH) and triphenylamine (TPA-PH)) were synthesized and demonstrated fluorophore unit dependent fluorescence photoswitching and mechanofluorochromism. TPE-PH and TPA-PH exhibited reversible off–on and dual-state fluorescence photoswitching, respectively, due to conformational changes upon light irradiation. In contrast, PY-PH showed irreversible photoswitching. Further, TPA-PH displayed fluorescence switching between two fluorescence states whereas TPE-PH showed off–on switching upon crushing and heating. PY-PH did not show clear mechanofluorochromism. Thus, the present work explored the structural impact on the fluorescence photoswitching and mechanofluorochromism that might be useful for developing new photofluorochromic/mechanofluorochromic smart materials for multifunctional applications.

Graphical abstract: Fluorophore unit controlled photoswitching of hydrazone derivatives: reversible and irreversible off–on/dual-color fluorescence photoswitches

Supplementary files

Article information

Article type
Paper
Submitted
09 Jun 2023
Accepted
27 Jul 2023
First published
27 Jul 2023

Mol. Syst. Des. Eng., 2023,8, 1462-1469

Fluorophore unit controlled photoswitching of hydrazone derivatives: reversible and irreversible off–on/dual-color fluorescence photoswitches

D. K. Sivadas, S. Ravi, P. Nagarasu, D. Johnson, V. Thiruvenkatam, S. P. Anthony and V. Madhu, Mol. Syst. Des. Eng., 2023, 8, 1462 DOI: 10.1039/D3ME00093A

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