1234622-42-4Relevant articles and documents
Synthesis and chemical properties of diacetylenes with pyridinium and 4,4′-bipyridinium groups
Yamaguchi, Isao,Higashi, Hideo,Kimura, Shunsuke,Sato, Moriyuki
, p. 819 - 828 (2010)
Diacetylenes (DAs) having a dipolar D-π-A structure (D = donor: amino group; π = π-conjugation core; A = acceptor: pyridinium (Py) and bipyridinium (BPy) groups), i.e., 4 (APBPyDA) and 5 (APPyPyDA), or an A-π-A structure, i.e., 7 (DBPyDA) and 8 (PyDA(Cl)), were obtained by 1 : 1 and 1 : 2 reactions of 4,4′-(buta-1,3-diyne-1,4-diyl)bis[benzenamine] (APDA; 3) with 1-(2,4-dinitrophenyl)-1′-hexyl-4,4′-bipyridinium bromide chloride (1 : 1 : 1) (1), 1-(2,4-dinitrophenyl)-4-(pyridin-4-yl)pyridinium chloride (2), or 1-(2,4-dinitrophenyl)pyridinium chloride (6) (Schemes 1 and 2). The anion-exchange reactions of 8 with NaI and Li(TCNQ) (TCNQ-=2, 2′-(cyclohexa-2,5-diene-1,4-diylidene)bis[propanedinitrile] radical ion (1-)) yielded the corresponding I- and TCNQ- salts 9 (PyDA(I)) and 10 (PyDA(TCNQ)). Compounds 10 and 4 exhibited a UV/VIS absorption due to a charge transfer between the TCNQ- and the pyridinium groups and a strong solute - solvent interaction of a dipolar solute molecule in the polar environment, respectively. Compounds 8-10 exhibited photoluminescence in solution, whereas 4 and 7 did not because of the presence of the 4,4′-bipyridinium quenching groups. Differential-scanning-calorimetry (DSC) measurements suggested that the DAs obtained in this study can be converted into poly(diacetylenes) by thermal polymerization.