Acceptor-π-Acceptor-Acceptor/Donor systems containing dicyanovinyl acceptor group with substituted 1,2,3-triazole motif - synthesis, photophysical and theoretical studies

An efficient synthetic route (target products obtained with yields 65-85%) for obtaining of malononitrile derivatives containing triazole motif substituted in the way providing the electronic architecture Acceptor-pi-Acceptor-Acceptor/Donor (-CH2(CN)(2)/-C6H4-/triazole/substituent) is presented. As the substituents phenyl (Al), p-pentyloxyphenyl (A2), pyrid-2-yl (A3), 9,9-dimethylfluoren-2-yl (A4), 9octyl-9H-carbazol-3-yl (A5), dibenzo[b,dithiophen-2-yl (A6) and 2,2'-bithiophenyl-5-yl (A7) were used. The structures of compounds were confirmed by H-1 and C-13 NMR spectroscopy. The thermal, optical and photophysical properties of obtained target compounds were checked. Understanding of obtained data was supported by quantum-chemical calculations based on DFT methods (time-dependent calculations, NTO analysis, structural parameters). Moreover, the druglikeness analysis was performed based on the commonly known rules. (C) 2019 Elsevier B.V. All rights reserved.