Design and synthesis of disubstituted and trisubstituted thiazoles as multifunctional fluorophores with large Stokes shifts

Synthesis and Spectrophotometric Studies of 9‐Substituted‐4,5‐dimethoxyacridine Multifunctionalizable Fluorescent Dyes and Their Macrocyclic Derivatives

“…A study on 4,5‐dimethoxyacridone ( 12 ) indicated that methoxy groups reduced quantum yield compared to the unsubstituted acridone ( 2 ) (0.410→0.100). All of the fluorescent compounds showed extremely large Stokes ‐shifts compared to the reported dyes [46–54] . This advantageous photophysical property can reduce interferences from self‐absorption and auto‐fluorescence, thus provides outstanding sensitivity and resolution for optochemical devices.…”

“…All of the fluorescent compounds showed extremely large Stokes-shifts compared to the reported dyes. [46][47][48][49][50][51][52][53][54] This advantageous photophysical property can reduce interferences from self-absorption and autofluorescence, thus provides outstanding sensitivity and resolution for optochemical devices. Compounds with large Stokesshifts, especially functionalizable-group-containing derivatives, which are reported herein, can have great importance for practical applications and are in the focus of very recent research activities.…”

“…Compounds with large Stokesshifts, especially functionalizable-group-containing derivatives, which are reported herein, can have great importance for practical applications and are in the focus of very recent research activities. [46][47][48][49][50][51][52][53][54] Although studies on photophysical behavior of the new fluorescent precursors were carried out primarily from the aspect of the nature of the substituent at position 9 of acridine, it should be noted that fluorescence properties of acridine dyes strongly depend on the polarity of the medium as well as on the hydrogen-bonding ability of the solvent (they generally have weak fluorescence in apolar solvents and strong fluorescence in protic solvents). [45,55,56] Moreover, the protonated forms of these weak bases usually have spectral features quite different than those of the corresponding neutral forms.…”

Asymmetric Dual‐State Emitters Featuring Thiazole Acceptors

“…[9,13] Some of these thiazole derivatives have been used in WOLEDs, [14] solar cells, [15] OFETs, and OPVs. [16] It is also important to mention that most synthetic methods afford either 2,4,5-trisubstituted [10,17] or 2,4-disubstituted thiazoles, [18] and that fluorophores with 2,5-disubstituted thiazoles are very scarce, with some notable examples reported as DSEgens. [9,19] In this work, we present the design and synthesis of a new series of fluorophores 7-11 featuring a thiazole acceptor as well as the study of their corresponding photophysical properties in solution and in the solid-state.…”

Two Approaches for the Synthesis of Fused Dihydropyridines via a 1,6-Electrocyclic Reaction: Fluorescent Properties and Prospects for Application

“…Thioamides are building blocks widely used for the synthesis of nitrogen- and sulfur-containing heterocyclic compounds. − Thioamides can react with various monoelectrophilic, dielectrophilic, and ambient agents, such as α-halocarbonyl compounds and alkyl and alkenyl dihalides. − The CS bond of a thioamide group may react as a dienophile component in [4 + 2] cycloaddition reactions − and as a dipolarophile in the thermal and catalytic variants of 1,3-dipolar cycloaddition reactions. ,, Moreover, α-diazothioacetamides easily transform into 1,2,3-thiadiazoles by a 1,5-electrocyclic reaction. ,− …”