Issue 97, 2016

Solvent dependent isomerization of photochromic dithienylethenes: synthesis, photochromism, and self-assembly

Abstract

A series of photochromic dithienylethene incorporated with phenol (DTE1), catechol (DTE2), azophenol (DTE3) groups was synthesized and characterized by means of NMR spectroscopy, mass spectrometry and elemental analysis. The photophysical, photochromic and photoisomerization properties of molecules were studied using absorption and emission spectroscopies in different solvents. The cistrans photoisomerizations of azophenols in DTE3 compete with photocyclization of dithienylethene, resulting in low photoconversion yields in DTE3. Thermal isomerization of cis-azophenols was found to be solvent-dependent – a fast thermal relaxation from cis- to trans-isomer in chloroform, and a slow process in THF. For example in chloroform, formation of a closed-ring dithienylethene with trans-azophenols (trans-DTE3closed) was observed upon irradiation with UV light (365 nm). On the other hand, closed-ring dithienylethene with cis-azophenols (cis-DTE3closed) was formed in THF under the same condition. After forming a complex with Fe3+ ions, DTE2 showed a red shift of 27 nm in the absorption maximum. Scanning electron microscopy (SEM) analysis revealed formation of circular nanostructures with diameters in the range of 300–600 nm from DTE2closed film. Factors such as solvent, photoisomerization, and hydrogen bonding toward the formation of such supramolecular nanostructures and morphologies are discussed.

Graphical abstract: Solvent dependent isomerization of photochromic dithienylethenes: synthesis, photochromism, and self-assembly

Supplementary files

Article information

Article type
Paper
Submitted
25 Aug 2016
Accepted
28 Sep 2016
First published
28 Sep 2016

RSC Adv., 2016,6, 95137-95148

Solvent dependent isomerization of photochromic dithienylethenes: synthesis, photochromism, and self-assembly

C. P. Sen and S. Valiyaveettil, RSC Adv., 2016, 6, 95137 DOI: 10.1039/C6RA21348K

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