1,2,3-triazoles as conjugative pi-linkers in push-pull chromophores: importance of substituent positioning on intramolecular charge-transfer.

Clicks: 393
ID: 57916
2008
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Abstract
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 lambda(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.
Reference Key
jarowski2008123triazolesorganic Use this key to autocite in the manuscript while using SciMatic Manuscript Manager or Thesis Manager
Authors Jarowski, Peter D;Wu, Yi-Lin;Schweizer, W Bernd;Diederich, François;
Journal Organic letters
Year 2008
DOI
10.1021/ol801253z
URL
Keywords
annulation heterocycles synthetic methods reaction mechanisms rhodium

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