Synthesis of 5-aryl-5′-formyl-2,2′-bithiophenes as new precursors for nonlinear optical (NLO) materials

Abstract

Synthesis of 5-aryl-5´-formyl-2,2´-bithiophenes as new precursors for nonlinear optical (NLO) materials

New thiophene- and phenothiazine-containing chalcones: Synthesis, and electrochemical properties

“…Yield 75%, yellow crystals, solutions in CH 2 Cl 2 possess green fluorescence, mp 124-125°C (124-125°C [11]). UV spectrum, λ max , nm: 320, 400.…”

“…For preparation of these chalcones we have initially synthesized two already known methyl ketones I [11] and II [12], after that a thiophene fragment was introduced into their structure. At the first stage of the synthesis the Vilsmeier-Haak-Arnold reaction was carried out to prepare compounds III and IV, their cyclization with chloroacetone in the presence of Na 2 S afforded methyl ketones V and VI used further as methylene components in the synthesis of chalcones [11,13,14].Refluxing of the obtained methyl ketones V and VI with 4-(10N-phenothiazin-10-yl)-and 4-(9N-carbazol-9-yl)benzaldehydes VII and VIII in the alkaline alcohol solution gave rise to the target chalcones IX-XII. Thus prepared chalcones are the dark red or orange crystalline substances, well soluble in common organic solvents, and their solutions in dichloromethane possess a pronounced yellow and yellow-green fluorescence, and in hexane -a blue one.…”

“…For preparation of these chalcones we have initially synthesized two already known methyl ketones I [11] and II [12], after that a thiophene fragment was introduced into their structure. At the first stage of the synthesis the Vilsmeier-Haak-Arnold reaction was carried out to prepare compounds III and IV, their cyclization with chloroacetone in the presence of Na 2 S afforded methyl ketones V and VI used further as methylene components in the synthesis of chalcones [11,13,14].…”

Synthesis of Novel Arylazothiazolyl-thiophene Dyes for Solar Cell and Nonlinear Optical Materials

“…[10][11][12][13] Thiophene derivatives are versatile building blocks for the synthesis of donor-acceptor substituted π-conjugated systems for several optical applications. Recently, the synthesis of novel formyl π-conjugated systems (bithiophenes, 14 oligothiophenes, 15 arylthiophenes 16 and arylbithiophenes 17 ) has been reported through several methods of synthesis such as cross-coupling reactions (Stille, 15 Suzuki 16,17 ), metalation followed by quenching with DMF, 14 Vilsmeier-Haack formylation 18 and Vilsmeier-Haack Arnold reactions. 17 In the light of the previously mentioned literature, we decided to synthesize new N-(5-arylazothiazol-2-yl)-2-aminothiophene dyes to characterize their electrochemical properties and their viability in solar cells and nonlinear optical materials applications.…”

“…Recently, the synthesis of novel formyl π-conjugated systems (bithiophenes, 14 oligothiophenes, 15 arylthiophenes 16 and arylbithiophenes 17 ) has been reported through several methods of synthesis such as cross-coupling reactions (Stille, 15 Suzuki 16,17 ), metalation followed by quenching with DMF, 14 Vilsmeier-Haack formylation 18 and Vilsmeier-Haack Arnold reactions. 17 In the light of the previously mentioned literature, we decided to synthesize new N-(5-arylazothiazol-2-yl)-2-aminothiophene dyes to characterize their electrochemical properties and their viability in solar cells and nonlinear optical materials applications. In addition, the effect of increasing conjugation through the addition of thiophene unit and its influence on the optical and redox properties has been investigated.…”