2006
DOI: 10.1021/ol061277s
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Synthesis and Characterization of Dicyanovinyl-Substituted Thienylpyrroles as New Nonlinear Optical Chromophores

Abstract: [structure: see text] New dicyanovinyl-substituted 1-(alkyl)aryl-2-(2'-thienyl)pyrroles 2 were synthesized and characterized. The solvatochromic behavior of the synthesized compounds was investigated. All the derivatives showed reversible oxidation and reduction on the CV time scale. The hyperpolarizabilities (beta) of compounds 2 were measured using hyper-Rayleigh scattering. The results are among the highest beta values reported for donor-acceptor-substituted thienylpyrroles.

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Cited by 106 publications
(45 citation statements)
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“…In the design of a conjugated p-system between donor and acceptor moieties in push-pull molecules, the incorporation of aromatic five-membered heterocycles has received much attention and often results in enhanced first molecular hyperpolarizability [8][9][10][11][12][13][14][15][16][17][18]. However, a delicate interplay of various factors must be taken into account; on the one hand, the aromaticity of the heterocycle is obviously important in providing efficient electron transfer between donor and acceptor moieties whilst, in contrast, it is clear that the electronic nature of the heteroaromatic ring will determine whether it acts as an ''auxiliary donor'' or an ''auxiliary acceptor'' [19].…”
Section: Introductionmentioning
confidence: 99%
“…In the design of a conjugated p-system between donor and acceptor moieties in push-pull molecules, the incorporation of aromatic five-membered heterocycles has received much attention and often results in enhanced first molecular hyperpolarizability [8][9][10][11][12][13][14][15][16][17][18]. However, a delicate interplay of various factors must be taken into account; on the one hand, the aromaticity of the heterocycle is obviously important in providing efficient electron transfer between donor and acceptor moieties whilst, in contrast, it is clear that the electronic nature of the heteroaromatic ring will determine whether it acts as an ''auxiliary donor'' or an ''auxiliary acceptor'' [19].…”
Section: Introductionmentioning
confidence: 99%
“…spectra is observed when stronger acceptor groups are linked to the heterocyclic system. [8][9][10][11][12][19][20] As a result the substitution of a formyl group for a 2-(3-oxo-2,3-dihydroinden-1-ylidene)malononitrile moiety leads to a red shift of 170 nm from 348 nm (1a) to 510 nm (1e). Within the series 1a-e the CT bands moves to lower energy as the electron accepting ability of the acceptor moiety increases, in the order CHO < dicyanovinyl < rhodanine < thiobarbituric acid < 2-(3-oxo-2,3-dihydroinden-1-ylidene)malononitrile (Fig.…”
Section: Linear and Nonlinear Optical Properties Of The Chromophoresmentioning
confidence: 99%
“…Recently we were able to overcome these difficulties and reported on the interesting electrochemical and solvatochromic properties and the first hyperpolarizabilities of pyrrolecontaining NLO chromophores with potential application as nonlinear optical compounds. [8][9][10][11][12] We were therefore motivated to extend these studies and explore the potential of a novel series 1-(4-(thiophen-2-yl)phenyl)-1H-pyrroles 1 as efficient push-pull systems bearing pyrrole as donor group and dicyanovinyl, rhodanine, thiobarbituric acid and indanonedicyanovinyl as acceptor moieties linked through an arylthiophene spacer.…”
Section: Introductionmentioning
confidence: 99%
“…Considerable research efforts have been given to the preparation of transition metal complexes of hybrid ligands because they can provide new materials with useful properties such as magnetic exchange [1][2][3][4], electrical conductivity [5,6], photoluminescence [7][8][9], non-linear optical property [10][11][12] and antimicrobial activity [13,14]. Among various ligands azo group containing ligands have received much attention in recent years.…”
Section: Introductionmentioning
confidence: 99%