Synthesis and Relative Thermal Stabilities of Diphenylamino- vs Piperidinyl-Substituted Bithiophene Chromophores for Nonlinear Optical Materials

Bedworth, Peter V.; Cai, Yuankun; Jen, Alex K.‐Y.; Marder, Seth R.

doi:10.1021/jo9517555

Cited by 108 publications

(69 citation statements)

References 7 publications

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“…Starting bromoaldehydes 5a, c are available commercially, while 5b was prepared from 2-bromothiophene according to an earlier published procedure [24]. Bromoaldehydes 5a-c were converted to the corresponding 4-(dimethylamino)-phenyl aldehydes 4a-c by Suzuki coupling with commercially available 4-(dimethylamino)phenylboronic acid 6.…”

Section: Synthesismentioning

confidence: 99%

Push–pull chromophores comprising benzothiazolium acceptor and thiophene auxiliary donor moieties: Synthesis, structure, linear and quadratic non-linear optical properties

et al. 2009

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a b s t r a c tNovel, push-pull chromophores combining a cationic benzothiazolium acceptor moiety and either one or two thiophene rings as a part of the conjugated p-system between the donor and the acceptor moieties have been synthesized and characterized. The chromophores displayed pronounced quadratic NLO activity with their first molecular hyper polarizabilities in agreement with their linear spectral properties.

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Section: Synthesismentioning

confidence: 99%

Push–pull chromophores comprising benzothiazolium acceptor and thiophene auxiliary donor moieties: Synthesis, structure, linear and quadratic non-linear optical properties

et al. 2009

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“…[1][2][3] It has been revealed that the second order hyperpolarizabilities (β) of heterocyclic chromophores are often higher than their benzene analogues. [4][5][6][7][8][9][10][11][12] Recently we have also demonstrated that donor-acceptor substituted bithiophenes and terthiophenes have many favorable features as NLO materials. [13][14][15][16] Conjugated thiophene and pyrrole derivatives as donors combined with substituted acceptor groups are promising candidates among such D-A systems due to their numerous applications.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of tricyanovinyl-substituted thienylpyrroles and characterization of the solvatochromic, electrochemical and non-linear optical properties

et al. 2005

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-Tricyanovinyl-substituted 1-(alkyl)aryl-2-(2´-thienyl)pyrroles 1 have been synthesized by direct tricyanovinylation reaction of 1-(alkyl)aryl-2-(2´-thienyl)pyrroles 2 using TCNE. The tricyanovinyl-derivatives 1 display dramatic reductions in both their optical and electrochemical band gaps relative to thienylpyrrole precursors 2. The solvatochromic behavior of compounds 1 was investigated in a variety of solvents. Hyper-Rayleigh scattering was used to measure the first hyperpolarizabilities β of the mentioned compounds. The β values show that the new compounds prepared could be used on the manufacture of materials with good non-linear (NLO) properties.

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“…11 This route allowed to prepare a large variety of N,N-disubtituted 2-aminothiophenes 7 but it gives in several cases only low yields of products. 12 Therefore, another synthetic route to the target compounds was an advantageous alternative. It was developed by us recently and consists in a heterocyclisation reaction starting from simple N,N-disubtituted acetamides 11.…”

Section: Methodsmentioning

confidence: 99%

On the Vilsmeier formylation of N-aryl-substituted 2-aminothiophenes - a simple route to new thieno[2,3-b]quinolinium salts

Hartmann¹

2012

Arkivoc

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The Vilsmeier reaction of N-substituted 2-arylamino-thiophenes-5-carboxylic acid or their alkyl derivatives gives rise, depending on the substitution pattern at the thiophene moiety, to the formation of either N-substituted 2-arylamino-thiophene-5-carbaldehydes, corresponding imminium salt precursors, or novel thieno[2,3-b]quinolinium salts. These salts are highly reactive towards nucleophiles and can be easily transformed by reduction into the corresponding 4,9-dihydro derivatives.

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Synthesis and Relative Thermal Stabilities of Diphenylamino- vs Piperidinyl-Substituted Bithiophene Chromophores for Nonlinear Optical Materials

Cited by 108 publications

References 7 publications

Push–pull chromophores comprising benzothiazolium acceptor and thiophene auxiliary donor moieties: Synthesis, structure, linear and quadratic non-linear optical properties

Push–pull chromophores comprising benzothiazolium acceptor and thiophene auxiliary donor moieties: Synthesis, structure, linear and quadratic non-linear optical properties

Synthesis of tricyanovinyl-substituted thienylpyrroles and characterization of the solvatochromic, electrochemical and non-linear optical properties

On the Vilsmeier formylation of N-aryl-substituted 2-aminothiophenes - a simple route to new thieno[2,3-b]quinolinium salts

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