An iminodibenzyl–quinoxaline–iminodibenzyl scaffold as a mechanochromic and dual emitter: donor and bridge effects on optical properties

Abstract

Dual emission (TADF + RTP) and mechanochromism have been obtained using an iminodibenzyl–quinoxaline–iminodibenzyl scaffold.

Reversibly Switchable Phase‐Dependent Emission of Quinoline and Phenothiazine Derivatives towards Applications in Optical Sensing and Information Multicoding

“…A 10 wt % solid dispersion of PZPQ in Zeonex was prepared for testing the oxygen sensitivity of the compound. Zeonex was used as a rigid matrix to suppress intermolecular interactions [37–39] and leave the energy transfer to the oxygen molecules as the main path of nonradiative deactivation of excitons and exclude energy transfer between conformers. PL spectra were recorded consecutively under conditions of different nitrogen/oxygen ratios maintained for 15 min each for the stabilization of intensity.…”

Recent Developments on Multi-Functional Metal-Free Mechanochromic Luminescence and Thermally Activated Delayed Fluorescence Organic Materials

“…N.B . All photophysical studies in toluene Rajamalli et al, 2016 ; Ganesan et al, 2017 ; all photophysical studied on neat film Chen et al, 2018 ; Zhan et al, 2019 ; all photophysical studies in DCM Takeda et al, 2018 ; all photophysical studies in their respective solid states/crystalline states (Zhang et al, 2017 ; Huang et al, 2018 ; Data et al, 2019 ; Zheng et al, 2019a ); only UV/PL in toluene (Okazaki et al, 2017 ; Pashazadeh et al, 2018b ; Zeng et al, 2018 ; Zheng et al, 2019b ); only UV/PL in DCM Ishimatsu et al, 2014 ; Pashazadeh et al, 2018a ; life time study on thin film (CBP host) Zeng et al, 2018 ; Zheng et al, 2019b ; life time study on thin film (zeonex host) (Pashazadeh et al, 2018a , b ) .…”

“…Tashazadeh et al reported four new derivatives of quinoxaline-containing iminodibenzyl and iminostilbene moieties with TADF, RTP, and MCL properties (shown in Figure 13 ) (Pashazadeh et al, 2018a ). To perceive RTP and TADF simultaneously, a modest singlet–triplet energy splitting is required to tune the RISC rate, to directly harvest all the triplet excitons (phosphorescence).…”

“…(B) DF intensity vs. laser pulse energy plot of OIDBQx (at 295 K); (C) PL decay transients of OIDBQx at different temperature; (D) DF and RTP spectra (at 295 K) with different excitation pulse energy. Reproduced with permission from Pashazadeh et al ( 2018a ). Copyright © The Royal Society of Chemistry.…”

Preparation and Photoluminescent Properties of Three 5‐Amino Benzothiadiazoles (5‐amBTDs)

“…In our previous reports, the butterfly‐shaped 5,6‐disubstituted BTDs tended to crystalize much easier than the linear‐shaped 4,7‐disubstituted BTDs and finely tuned the emissive light of the bright crystals ranging from 473 nm to 627 nm by simply changing the substituted groups [4] . In the screening of the various donors by surfing the literature, azepane, [5] was selected in this study for its easier structural modification by installing phenyl groups, [6] the magnified absorptivity in comparison with other nitrogen‐containing rings, such as aziridine, azetidine, pyrrolidine and piperidine [7] and so far their multiple achievements in thermally activated delayed fluorescence emitter, [8] dye‐sensitized solar cell, [9] polymer LEDs [10] and the ultrasensitive fluorescence sensor [11] . Combining with our previous works on benzothiadiazole (BTD) on the development of new fluorescent compounds for optoelectronic materials and fluorescent probes, [12] azepane (AP), iminodubenzyl (IDB) and iminostilbene (ISB) were respectively installed on 5‐position of BTD, affording compounds 1 , 2 and 3 for the systematical investigation of the fluorescent structure‐property relationship (FSPR).…”