Microwave-assisted synthesis of 4-(2,2'-bithiophen-5-yl)-5-phenylpyrimidine derivatives as sensors for detection of nitroaromatic explosives

New V-shaped 2,4-di(hetero)arylpyrimidine push-pull systems: Synthesis, solvatochromism and sensitivity towards nitroaromatic compounds

“…S23 and S24, Table S1). In addition, the highest values of DL and Ksv were found for picric and styphnic acids, that was commonly observed for similar pyrimidine push-pull systems [16][17][18][19][20][21].…”

“…To evaluate an ability of fluorophores 5a-d to detect nitroaromatics and 2,3-dimethyl-2,3-dinitrobutane (DDBu), a common tag required by law for all commercial NATO plastic explosives, fluorescencequenching measurements in acetonitrile solutions containing measured quantities of different nitroaromatic compounds have been carried out using a well-known procedure [16][17][18][19][20][21] (Fig. 7).…”

“…Recently, the straightforward synthesis of the series of 4-(hetero)aryl (I), 4,5-di (hetero)aryl (II) and 4,5,6-tri(hetero)aryl (III) substituted pyrimidines by using the methodology of nucleophilic aromatic substitution (the S N H protocol) [15] has been described, and these structures can be applied for effective detection of various nitroaromatic explosives (see Fig. 1) [16][17][18][19][20][21].…”

Recent Advances in Direct C–H Functionalization of Pyrimidines

“…In fact, the various combinations of these two types of C-C coupling reactions, addition-oxidation S N H (AO) or addition-elimination S N H (AE), and also various sequences of steps have been used to obtain 4-(hetero)aryl-76, 5-bromo-4-(hetero)aryl-77, 5-(hetero)aryl-78, or 4,5-di(hetero)aryl-substituted pyrimidines 79 (Scheme 36). This protocol has been applied to the synthesis of a variety of antibacterial C4 and/or C5 pyrimidines [116][117][118][119]121 and new linear 80 and V-shaped 81 and 82 push-pull systems as dyes for solar cells 122,123 or chemosensors for detection of nitroaromatic compounds [124][125][126][127][128] (Scheme 37).…”

New "turn-off" fluorescence sensors to detect vapors of nitro-explosives on the basis of 4,6-bis[5-(heteroaryl)thiophen-2-yl] substituted 5-(4-tert-butylphenyl)pyrimidines

“…Such structures have been used as promising sensing materials for detection of a variety of nitroaromatics through fluorescence quenching. [33][34][35][36][37][38][39][40] As a part of our research studies on pyrimidine-based π-conjugated systems, we envisaged that mixed π-conjugated 4,6-bis[5-(heteroaryl)-thiophen-2-yl]-5-(4-tert-butylphenyl) pyrimidines, consisting of the electrondonating part, presented by triphenylamine, carbazole or pyrene fragments, and the electron-withdrawing pyrimidine unit, would be a new class of push-pull fluorophores with improved sensitivity towards nitroaromatic compounds. Indeed, we have been motivated to synthesize D-π-A-π-D conjugates 7a-c, in which electrondonating groups are attached to 4-and 6-positions of the pyrimidine ring via the thiophene spacer and 4-tertbutylphenyl substituent is incorporated at C-5 of pyrimidines.…”