Substitution effect on the photochromic properties of benzo[b]thiophene-1,1-dioxide based diarylethenes

Abstract

Benzo[b]thiophene-1,1-dioxide based diarylethenes (DAEs), BTT-1 to BTT-4, containing methyl, phenyl, formyl and triphenylamine groups at the 5,5'-position of thiophene rings have been developed for insight into substituent effects on the absorption and photochromic properties. Electron-donating substituents, such as phenyl and triphenylamine groups, are found to be effective to shift the absorption band to a longer wavelength and to decrease the cyclization quantum yield.Electron-withdrawing formyl group can increase the cyclization quantum yield, but reduce the thermal stability of the ringclosed isomer to some extent. BTT-4 bearing a triphenylamine group shows the poorest fatigue resistance among these four compounds, which is possibly due to the larger extended π-conjugation length in the ring-closed isomer. BTT-2 bearing a phenyl unit undergoes typical photochromic reaction not only in solution, but also in the PMMA thin film and in the bulky crystals with excellent fatigue resistance and thermal stability.

Synthesis, Photophysical, Photochromic, and Photomodulated Resistive Memory Studies of Dithienylethene-Containing Copper(I) Diimine Complexes

“…With its ongoing attraction and flourishing development in photocontrollable chemical reactivity, optoelectronics, and nanomaterials, the demand for the design of novel photoresponsive dithienylethene systems is foreseeable. To facilitate the rapid photoswitching efficiency and robust thermal stability, attempts to incorporate different heterocycles as the ethene backbone have been made , and those with weak aromaticity have been demonstrated to be outstanding candidates . In addition, tuning the photochromic properties via the coordination of dithienylethene-containing ligands to various metal centers − or heteroatoms has also been considered to be an effective approach by which a pronounced perturbation of the photochromic behavior can be achieved with the ease of structural derivatization. , …”

A fluorescent photochromic diarylethene based on naphthalic anhydride with strong solvatochromism

“…[1][2][3][4][5][6] In particular, diarylethene compounds exhibiting uorescence modulation properties, in which the uorescence could be switched on and off reversibly via the photochromic isomerization between the open-and closed-ring isomers, are desirable for their potential applications in logic gates, information storage and biological sensing by taking the advantages of uorescence such as sensitivity, convenience, and relative cheapness. [7][8][9][10][11][12][13] Rational molecular structure designs, whether on the side chains or the ethene bridge of the diarylethenes, aiming at regulating the uorescence have been well reported. [14][15][16][17][18][19][20][21][22] One of the efficient approaches is to replace the traditional ethene bridges (usually peruorocyclopentene or cyclopentene) with new aromatic uorophore building blocks.…”