66251
PTDC/QUI/66251/2006
FCT - Fundação para a Ciência e a Tecnologia, I.P.
Portugal
5876-PPCDTI
159,486.00 €
2009-01-01
2012-12-31
A series of heterocyclic azo dyes was synthesized by diazotation of several substituted anilines and coupling with 5-N,N-dialkylamino-2,2´-bithiophenes to give 4-phenylazo-5-N,N-dialkylamino-2,2´-bithiophenes 4-7. This reaction contrasts with the behavior of 5-alkoxy-2,2´-bithiophenes towards aryldiazonium salts which gave 5-phenylazo-5-alkoxy-2,2´-bithiophenes. The thermal stability of the derivatives was eval...
A series of formyl-substituted 5-aryl-2,2´-bithiophenes 5 were synthesized using two different methods: Vilsmeier-Haack-Arnold reaction (VHA) or through Suzuki coupling. The synthesis of compounds 5 through the Vilsmeier-Haack-Arnold reaction, starting from inexpensive and easily available precursors such as acetophenones, gave the title compounds in low yields after four reaction steps. On the other hand Suzuk...
A detailed spectroscopic and photophysical study has been carried out on a series of heterocyclic compounds -known to display nonlinear optical properties- consisting on one electron donating thienylpyrrolyl π-conjugated system functionalized with an electron acceptor benzothiazole moiety. The absorption, emission and triplet-triplet absorption together with all relevant quantum yields (fluorescence, intersyste...
Two series of dicyanovinyl-substituted compounds namely 2-aryl-5-dicyanovinyl-thiophenes 4 and 5-aryl-5´-dicyanovinyl-2,2´-bithiophenes 6 were synthesized through Knoevenagel condensation of the corresponding 2-aryl-5-formyl-thiophenes 3 and 5-aryl-5´-formyl-2,2´-bithiophene 5 precursors. On the other hand, precursors 3 were prepared through the Vilsmeier-Haack-Arnold reaction (VHA) starting from inexpensive an...
A series of novel donor-acceptor chromophores designed to have good second order nonlinear optical responses has been synthesized and characterized. This series of compounds was designed to explore the consequence of using different electron accepting moieties which were linked through an arylthiophene bridge to a pyrrole heterocycle that plays the role of an auxiliary donor group. These new push-pull chromopho...
Two series of novel push-pull heterocyclic azo dyes have been synthesized and characterized. The two series of compounds were based on different combinations of π-conjugated bridges (bithiophene and thienylpyrrole) which also act simultaneously as donor groups, together with diazo(benzo)thiazolyl as acceptor moieties. Their thermal stability and electrochemical behavior were characterized, while hyper-Rayleigh ...
Quaternized pyridine derivatives have attracted interest for many years from various perspectives, especially for potential applications in electronic/optical devices.1 Pyridinium salts are readily synthesized, highly stable, and often combine intense visible absorptions with reversible electrochemistry. Notable recently proposed applications of these compounds range from advanced telecommunications to fluoresc...
The synthesis and characterization of new chromophores with second-order nonlinearities containing thienylpyrrole 1a, 2a-b, bithiophene 3 and arylthiophene 4 as π-conjugated bridges and indanonedicyanovinyl acceptor group are reported. The effect of placing the acceptor group at thiophene or pyrrole rings on the optoelectronic properties was also evaluated for thienylpyrrole derivatives 1a and 2a-b. The linear ...
Three series of bithiophene azo dyes functionalized with thiazol-2-yl or benzothiazol-2-yl-diazene acceptor moieties were synthesized through azo coupling reaction using 2,2´-bithiophene, 5-alkoxy-2,2´-bithiophenes, 5-N,N-dialkylamino-2,2´-bithiophenes and thiazolyl and benzothiazolyl diazonium salts as coupling components. The 5-alkoxy-2,2´-bithiophene precursors yielded the 5-thiazolylazo-5´-alkoxy-2,2´-bithi...
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