Quinoline-containing diarylethenes: bridging between turn-on fluorescence, RGB switching and room temperature phosphorescence

Abstract

Simple structural modifications using oxidation and methylation of a quinoline-containing diarylethene result in dramatic variation of photophysical properties.

Dual emission in purely organic materials for optoelectronic applications

“…16 was demonstrated to be a potential fluorophore for super-resolution imaging, and also a rare example of a singlecomponent red-blue pH switching material, reminiscent of litmus indicator but in emission rather than reflection. 24 In all the above examples, the observed PF DE was the result of photoexcitation of an isolated molecule. However, some molecules emit upon aggregation (AIE) 67,68 or upon the formation of an excited state complex (excimer or exciplex).…”

“…In contrast, in ICT materials the equilibrium of a parent LE state and a twisted intramolecular charge transfer (TICT) state represents the most common case of dual fluorescence, 20 although singlet DE can also originate from the existence of dual CT states, 21 excimer states, 22 excited state intramolecular proton transfer (ESIPT) 23 and structural modification of the emitter upon absorption of UV light. 24 However, DE in a single molecule can also be achieved with the involvement of states of different multiplicity. An appropriate balance of emission and intersystem crossing (ISC) rates can generate coexisting populations of singlet and triplet states, both of which are sensitive to molecular structure and the environment.…”

A Photo‐ and Redox‐Driven Two‐Directional Terthiazole‐Based Switch: A Combined Experimental and Computational Investigation

“…[16][17][18][19] Compared to diarylethenes with classical central ethene moieties such as perfluorocyclopentene, cyclopentene and maleimide etc., [2] the central aryl group offers an extra site available for further functionalization of the switch in addition to the two lateral aryl groups. [20][21][22] For instance, we have shown that a properly designed terthiazolylene could act as photochromic ligand and give rise to metal complexes with interesting photo-responsive properties. [23] With regard to redox-responsive behavior, different terarylenes (aryl = thiazolyl, thienyl group or a combination of the two) have been reported to undergo oxidation induced ring-opening of their respective closed forms and, moreover, this ring-opening reaction was found to proceed via an auto-catalytic chain reaction mechanism with an efficiency well above 100 %, [24,25] but no reductive cyclization is known for terarylenes, to our knowledge.…”

Persistent Room‐Temperature Phosphorescence from Purely Organic Molecules and Multi‐Component Systems

“…reported diarylethene luminophores 1o , 2o , and 3 containing quinoline moieties ( Figure a). [ 64 ] Compound 1o shows typical diarylethene photocyclization character in CH 2 Cl 2 solution when irradiated by 365 nm UV, with its color turning from colorless in the open form to red in the closed form. Phosphor 3 is achieved by methylation of the quinoline nitrogen of 1o .…”