Stiff‐Stilbene Photoswitches: From Fundamental Studies to Emergent Applications

Abstract

Stiff‐stilbene, a sterically restricted fused ring analogue of stilbene, has been regularly used as a model compound in theoretical studies of stilbene photoisomerization. Lately, owing to its excellent photoswitching properties, it is increasingly being applied to reversibly control the properties and function of chemical as well as biological systems. Stiff‐stilbene photoswitches possess a number of advantageous properties including a high quantum yield for photoisomerization and a high thermal stability. Furthermore, they undergo a large geometrical change upon isomerization and their synthesis is straightforward. Herein, we provide an overview of the basic properties of stiff‐stilbene and of recent applications in supramolecular chemistry, catalysis, and biological systems.

Photoresponsive molecular tools for emerging applications of light in medicine

“…1). Azobenzenes 6 and their heteroaromatic analogues, 7 indigos, 8 hemithioindigos, 9 stilbenes, 10 hydrazones, 11 and iminothioindoxyls 12 undergo the double bond isomerisation, while diarylethenes 13 switch via the 6p electrocyclization. Spiropyrans 14 follow a mixed mechanism, as they rst undergo 6p electrocyclization, and later the trans-cis isomerization takes places.…”

More Than Resveratrol: New Insights into Stilbene-Based Compounds

“…Stiff-stilbenes (1,1 -diindanylidene), a fuse ring analogue of the stilbene, have been widely explored as molecular rotors, molecular force probes, and optical switches [34]. This group has been regularly used as a model compound in theoretical studies of stilbene photoisomerization [35]. Stiff-stilbenes have drawn the attention of scientists mainly because of their important properties, such as (i) high quantum yield for photochemical isomerization, (ii) the high thermal stability of the Z isomer, (iii) the straightforward synthesis, and (iv) the large geometrical change upon isomerization [35].…”

“…This group has been regularly used as a model compound in theoretical studies of stilbene photoisomerization [35]. Stiff-stilbenes have drawn the attention of scientists mainly because of their important properties, such as (i) high quantum yield for photochemical isomerization, (ii) the high thermal stability of the Z isomer, (iii) the straightforward synthesis, and (iv) the large geometrical change upon isomerization [35]. All these advantages may be used to develop smart materials or new fluorophores [34,35].…”

“…Stiff-stilbenes have drawn the attention of scientists mainly because of their important properties, such as (i) high quantum yield for photochemical isomerization, (ii) the high thermal stability of the Z isomer, (iii) the straightforward synthesis, and (iv) the large geometrical change upon isomerization [35]. All these advantages may be used to develop smart materials or new fluorophores [34,35]. Moreover, it was found that stiff-stilbene may also be used to design selective anticancer and antiparasitic compounds [36].…”

Controlled Diffusion of Photoswitchable Receptors by Binding Antielectrostatic Phosphate Oligomers

“…Recently, some of us developed the first photoswitchable receptors exhibiting strong dihydrogen phosphate binding. [19] These receptors were based on molecular motor and stiff-stilbene scaffolds [20] containing urea anion binding motifs. These hosts could be converted from a weakly guest-binding E to a strongly binding Z form using near-UV light ( Figure 2).…”