1,2,3-Triazoles as conjugative π-linkers in push-pull chromophores: Importance of substituent positioning on intramolecular charge-transfer

Peter D. Jarowski; Yi Lin Wu; W. Bernd Schweizer; François Diederich

doi:10.1021/ol801253z

1,2,3-Triazoles as conjugative π-linkers in push-pull chromophores: Importance of substituent positioning on intramolecular charge-transfer

Peter D. Jarowski, Yi Lin Wu, W. Bernd Schweizer, François Diederich^*

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

85 Scopus citations

Abstract

(Chemical Equation Presented) Isomeric charge-transfer chromophores using 1,2,3-triazol-diyl as linker have been studied experimentally and computationally. The instability of the polarized reactants precluded the use of the Huisgen reaction and alternative synthetic methodologies were employed. Charge-transfer absorptions between an N,N-dimethylanilino and a dicyanovinyl group are modest to strong, with maxima from λ_max = 400 to 453 nm depending on substituent positioning. TD-B3LYP/6-31G(d) calculations are within 0.6 eV of experiment and assign these bands as HOMO-LUMO transitions.

Original language	English (US)
Pages (from-to)	3347-3350
Number of pages	4
Journal	Organic Letters
Volume	10
Issue number	15
DOIs	https://doi.org/10.1021/ol801253z
State	Published - Dec 1 2008

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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abstract = "(Chemical Equation Presented) Isomeric charge-transfer chromophores using 1,2,3-triazol-diyl as linker have been studied experimentally and computationally. The instability of the polarized reactants precluded the use of the Huisgen reaction and alternative synthetic methodologies were employed. Charge-transfer absorptions between an N,N-dimethylanilino and a dicyanovinyl group are modest to strong, with maxima from λmax = 400 to 453 nm depending on substituent positioning. TD-B3LYP/6-31G(d) calculations are within 0.6 eV of experiment and assign these bands as HOMO-LUMO transitions.",

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T1 - 1,2,3-Triazoles as conjugative π-linkers in push-pull chromophores

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AU - Jarowski, Peter D.

AU - Wu, Yi Lin

AU - Schweizer, W. Bernd

AU - Diederich, François

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AB - (Chemical Equation Presented) Isomeric charge-transfer chromophores using 1,2,3-triazol-diyl as linker have been studied experimentally and computationally. The instability of the polarized reactants precluded the use of the Huisgen reaction and alternative synthetic methodologies were employed. Charge-transfer absorptions between an N,N-dimethylanilino and a dicyanovinyl group are modest to strong, with maxima from λmax = 400 to 453 nm depending on substituent positioning. TD-B3LYP/6-31G(d) calculations are within 0.6 eV of experiment and assign these bands as HOMO-LUMO transitions.

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1,2,3-Triazoles as conjugative π-linkers in push-pull chromophores: Importance of substituent positioning on intramolecular charge-transfer

Abstract

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