Synthesis and specific solvatochromism of D-π-A type pyridinium dye

Article abstract of DOI:10.1016/j.tet.2012.08.010

Donor-π-acceptor (D-π-A) type pyridinium dye bearing an iodide ion as the counter anion that has been newly synthesized showed specific solvatochromism, leading to large bathochromic shift of absorption band in halogenated solvents: the bathochromic shifts of the D-π-A type pyridinium dye in halogenated solvents are larger than those of the non-halogenated solvents of low ε_r values. Investigation of absorption spectral measurement, ¹H NMR measurements, and semi-empirical molecular calculations (AM1 and INDO/S using the SCRF Onsager Model) revealed that the intramolecular charge transfer (ICT) characteristics of the D-π-A type pyridinium dye became stronger in the halogenated solvents. On the basis of the experimental results and the theoretical calculations, the influences of halogenated solvent on the large bathochromic shift of D-π-A type pyridinium dye are discussed. 2012 Elsevier Science. All rights reserved.