A photochromic prototype based on difurylperhydrocyclopentene with remarkable photoswitching behavior and in vivo application

Abstract

A new strategy has been developed to synthesize difurylperhydrocyclopentene derivatives. The compound displays reversible photochromism in solution and thin-film. The results show that furan is superior to thiophene in terms of strong fluorescence, higher photocyclization conversion and cyclization quantum yield, as well as better fatigue resistance. Owing to the molecule being derived absolutely from C, H, and O atoms, the compound exhibits no cytotoxicity, which enables it to potentially serve as a biodegradable and biorenewable material for in vivo applications.

A New Dicyano-vinyl Modified Difurylperhydrocyclopentene Photoswitch: Fluorescent Properties, Sensing Ability and in vivo Application

“…In comparison with compound BTE-c, it was found that the absorption maximum of compound BFE-c was shorter about 22 nm in acetonitrile solution. But the absorption maximum of compound BFE-c red-shifted about 152 nm compared to that of reported aldehyde-based difurylperhydrocyclopentene 1 [37] at the photostationary state due to the better conjugated structure of compound BFE. The emission peak at around 547 nm for compound BFE was also observed when it was excited at 386 nm ( Figure 1B) and its emission also exhibited a good response to UV light.…”

“…Compound BTE showed no fluorescence due to the less flexibility of furan ring, whereas the thiophene ring affected the non-radiative process. [26,37] Impressively, the emission of compound BFE red-shifted around 75 nm relative to that of compound 1 due to the strong ICT effect derived from cyano groups to bisfurylethene core in the molecule BFE.…”

“…Recently, a new type of difurylperhydrocyclopentene prepared by classic reactions in mild conditions was reported, showing that furan is superior to thiophene with regard to fluorescence properties, photocyclization conversion yield, better fatigue resistance and no cytotoxicity. [37] These results encouraged us to carry on the further structural modification of photochromic molecules on the strength of the furan moiety. Herein, a fluorescent photoswitch based on bisfurylethenes was subtly designed and facilely synthesized by the Knoevenagel condensation reaction.…”

The Endeavor of Diarylethenes: New Structures, High Performance, and Bright Future

“…Furan, however, would help with this dilemma and has been applied in several researches of single molecular photoswitching junctions . Apart from that, recent research on difurylperhydrocyclopentene has presented a furan based diarylethene derivative showing good emission and remarkable photoswitching performances . More interestingly, the furan based photoswitch possesses low cytotoxicity and holds a potential in photoswitchable fluorescent in vivo bioimaging reagent.…”

Functional polyimides based on diamine containing diarylethylene moieties and their photochromic mechanism studies

“…1 Therefore, they have great potential in various practical applications such as data storage, optoelectronic devices, sensing, tunable self-assembly morphology, super-resolution microscopy, anti-counterfeiting materials and other fields. [2][3][4][5][6] Among the family of photochromes, including spiropyran, 7 azobenzene, 8 Schiff-base, 9 triarylethylene [10][11][12] and dithienylethene (DTE), 13,14 DTE is regarded as the shining star due to its inherent bistable characteristics and excellent recyclability. Although in-depth research has been conducted on small molecule DTE materials, 15 their poor thermal stability, inferior film-forming property and easy oxidation nature are still the key constraints; however, by introducing DTE moieties into polymers, all issues can be resolved.…”