Ester-functionalized poly(3-alkylthienylene)s: substituent effects on the polymerization with FeCl3

Bizzarri, Paolo Costa; Andreani, F.; Casa, C. Della; Lanzi, Massimiliano; Salatelli, Elisabetta

doi:10.1016/0379-6779(95)03401-5

Cited by 50 publications

(22 citation statements)

References 14 publications

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“…In fact, a more intrinsic chromophore orientational order may be assumed for C 2 spacer-bearing copolymers because of their morerestricted movements with respect to the conjugated PT chain. [43][44][45] Moreover, the UV spectra show that copolymers P1 and P2 inhibit the setting up of high concentrations of A forms, so that in the high chromophoric absorption region the PT absorptions of the two copolymers are low. Therefore, the two absorption processes do not interfere very much with each other, which may favour NLO properties.…”

Section: Spectral Profiles and Nlo Propertiesmentioning

confidence: 98%

Electronic Transitions of Polyalkylthiophenes Partially Derivatized with NLO Chromophores: A Theoretical and Experimental Study

Lanzi

Bertinelli

Paganin

et al. 2006

Macro Chemistry & Physics

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Summary: The UV‐vis spectral profiles of some alkylthiophene copolymers in CHCl3 solutions, variously substituted with an azobenzenic NLO chromophore have been carefully analyzed and distinct intensity contributions have been assigned to the overlapped electronic transitions appearing in the lower energy part of the spectra. The different spectral behaviours are influenced by the chromophore content, the length of the alkylic side‐chain of the plastifying comonomer and, more significantly, by the number of the carbon atoms in the oligomethylenic spacer between the chromophoric group and the conjugated polythiophenic chain. This latter finding can be correlated with the strong steric hindrance caused by chromophore crowding in close proximity to the polymeric backbone. As the intensity distributions may be reasonably compared with the NLO properties, identification of the above parameters and of their role is an important step towards the synthesis of polyalkylthiophenes with predictable electronic properties and the development of materials with enhanced NLO characteristics.Graphical surfaces of the highest‐occupied (HOMO)s and the lowest unoccupied (LUMO) molecular orbitals involved in the first three π–π* electronic transitions of the chromophoric system.magnified imageGraphical surfaces of the highest‐occupied (HOMO)s and the lowest unoccupied (LUMO) molecular orbitals involved in the first three π–π* electronic transitions of the chromophoric system.

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Section: Spectral Profiles and Nlo Propertiesmentioning

confidence: 98%

Electronic Transitions of Polyalkylthiophenes Partially Derivatized with NLO Chromophores: A Theoretical and Experimental Study

Lanzi

Bertinelli

Paganin

et al. 2006

Macro Chemistry & Physics

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“…16 A polimerização química mais utilizada emprega haletos metá-licos como agente iniciador, sendo o cloreto férrico o mais utilizado com razão molar 4:1 (FeCl 3 :monômero) sob atmosfera inerte. [98][99][100][101][102][103][104][105] Politiofenos e derivados também podem ser obtidos através do acoplamento de Grignard (tipo Kumada), realizado a partir de monômeros 2,5-di-halogeniotiofeno 47 e derivados como mostrado na Figura 18. 3 Pomerantz e colaboradores 106 obtiveram polímeros derivados de tiofenos (dibromo-ésteres) através da reação de acoplamento de Ullmann, utilizando três equivalentes de cobre metálico em DMF, porém esta reação teve um tempo relativamente alto (7 dias), o que leva à conclusão de que o método oxidativo com FeCl 3 apresenta bons resultados com relação ao tempo de reação (cerca de algumas horas, tendo um máximo reportado de 24 h por alguns autores 107 ).…”

Section: Métodos Usuais De Obtenção De Politiofenos Síntese Química Dunclassified

Oligômeros e polímeros derivados do tiofeno: síntese e aplicações

Alves¹,

Calado²,

Matencio³

et al. 2010

Quím. Nova

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#Thanks a lot, Prof. Hans Viertler, for everything you taught me: a plenty of good chemistry, specially organic chemistry and electrochemistry… Thanks for the good examples to be followed and the mistakes and bad things to be avoided… and finally citing Carl Gustav Jung as followed, thank you for helping me to transform myself in the chemist I am now… " Recebido em 24/3/10; aceito em 27/8/10; publicado na web em 25/10/10 THIOPHENE-BASED OLIGOMERS AND POLYMERS: SYNTHESES AND APPLICATIONS. In this review we summarize recent synthetic investigations about the preparation of oligothiophenes and polythiophenes, the most important π-conjugated organic materials for applications in electrochromic and electroluminescent devices. It is showed that many interesting and novel functionalized oligothiophenes have been synthesized by convenient coupling strategies (Heck, Kumada, Negishi, Suzuki, Stille and Ullmann) and oxidative coupling methods. Synthesis of polythiophenes are also presented and described according to chemical and electrochemical polymerization methodologies. The description of these noteworthy synthetic methods illustrates how important and promising are the interdisciplinary approaches in the obtaining of oligothiophenes and polythiophenes.Keywords: oligomeric and polymeric thiophenes; syntheses; conjugated polymers. INTRODUÇÃOOs polímeros conjugados (PCs) são conhecidos como "metais sintéticos" devido a suas propriedades elétricas, magnéticas, eletrô-nicas e ópticas semelhantes aos dos metais; as propriedades de um polímero convencional (flexibilidade, processabilidade e formação de filmes finos, boa estabilidade térmica, etc.) e as propriedades de um semicondutor combinadas em um único material resultam em polímeros para aplicação no campo da eletrônica orgânica. A incontestável importância científica atual desta classe de materiais pode ser percebida pela concessão do Prêmio Nobel de Química de 2000 para Heeger, McDiarmid e Shirakawa por suas pesquisas com PCs. 1 É digno de nota que, quando estes materiais são estimulados eletricamente, podem ter sua cor variada de forma reversível ou mesmo emitir luz visível, o que possibilita a sua aplicação em diversos dispositivos eletrocrômicos 2 ou diodos emissores de luz orgânicos (OLEDs -Organic Light Emission Diodes). Dentre outras possibilidades de aplicação, pode-se citar o desenvolvimento de condutores elétricos, células fotovoltaicas poliméricas, transistores orgânicos, 3,4 anticorrosivos, 5,6 materiais eletrocrômicos, 7 baterias recarregáveis, 8 etc.Em meio aos diversos PCs pesquisados para o desenvolvimento dos dispositivos eletrônicos orgânicos, tais como politiofenos (1), polipirróis (2), polianilinas (3), 9,10 polifenilenovinilenos (4) 11 (Figura 1), destacam-se os politiofenos e seus derivados, que são os materiais mais estudados nesta área. 2 A possibilidade de aplicação dos politiofenos em dispositivos eletrocrômicos é conhecida desde 1983 12-15 e, em 1986, com a primeira síntese descrita de polialquiltiofenos com processabilidade e projeção a nível...

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“…Temperature was continuously monitored with a chromel± alumel thermocouple with its cold junction in direct contact with the sample holder. [5,11]. The method provides precipitation in situ of highly dispersed FeCl 3 , generally leading to complete monomer conversion and permitting a more homogeneous suspension of the polymer and lower molecular weights, as compared with the general method used for nonfunctionalized P3ATs [12].…”

Section: Instrumental Techniquesmentioning

confidence: 99%

Chromic effects in poly(3-(10-hexanoyloxydecyl)-2,5-thienylene) as precursor of ω-hydroxydecyl-functionalized polythiophen

Lanzi

Bertinelli²,

Costa-Bizzarri

et al. 1998

Polym. Adv. Technol.

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Ester-functionalized poly(3-alkylthienylene)s: substituent effects on the polymerization with FeCl3

Cited by 50 publications

References 14 publications

Electronic Transitions of Polyalkylthiophenes Partially Derivatized with NLO Chromophores: A Theoretical and Experimental Study

Electronic Transitions of Polyalkylthiophenes Partially Derivatized with NLO Chromophores: A Theoretical and Experimental Study

Oligômeros e polímeros derivados do tiofeno: síntese e aplicações

Chromic effects in poly(3-(10-hexanoyloxydecyl)-2,5-thienylene) as precursor of ω-hydroxydecyl-functionalized polythiophen

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