1,2,3-triazoles as conjugative pi-linkers in push-pull chromophores: importance of substituent positioning on intramolecular charge-transfer.
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.
Jarowski
Peter D
PD
Laboratorium für Organische Chemie, Eidgenössische Technische Hochschule, Hönggerberg, HCI, CH-8093 Zürich, Switzerland.
Wu
Yi-Lin
YL
Schweizer
W Bernd
WB
Diederich
François
F
D000814:Aniline Compounds / Q000737:chemistry*; D018360:Crystallography, X-Ray; D008958:Models, Molecular; D009570:Nitriles / Q000737:chemistry*; D013056:Spectrophotometry, Ultraviolet; D014230:Triazoles / Q000737:chemistry*; D014753:Vinyl Compounds / Q000737:chemistry
D000814:Aniline Compounds; D009570:Nitriles; D014230:Triazoles; D014753:Vinyl Compounds