89505-35-1Relevant academic research and scientific papers
Structure-activity relationship of new organic NLO materials based on push-pull azodyes. 1: Synthesis and molecular properties of the dyes
Tirelli,Altomare,Solaro,Ciardelli,Meier,Bosshard,Guenter
, p. 122 - 128 (2007/10/03)
Several new push-pull azobenzene dyes were synthesized by diazonium salt coupling of electron-poor anilines with N,N-dialkylanilines. Their dipole moments and first-order hyperpolarizabilities were evaluated respectively from the concentration dependence of the dielectric constant of solutions in apolar solvents and by the electric-field-induced-second-harmonic-generation (EFISH) technique. Investigation of the influence of both nature and steric hindrance of the electron-withdrawing group allowed to highlight a significant deviation from linearity in the relationship between dipole moments and first-order hyperpolarizabilities. This effect was particularly noticeable when multiple electron withdrawing groups pointing in different directions were present on the same phenyl ring. Johann Ambrosius Barth 1998.
THE EFFECTS OF CYCLIC TERMINAL GROUPS IN 4-AMINOAZOBENZENE AND RELATED AZO DYES. PART 1. ELECTRONIC ABSORPTION SPECTRA OF SOME MONOAZO DYES DERIVED FROM N-PHENYLPYRROLIDINE AND N-PHENYLPIPERIDINE
Hallas, Geoffrey,Marsden, Richard,Hepworth, John D.,Mason, Donald
, p. 149 - 154 (2007/10/02)
Monoazo dyes containing a terminal piperidino group absorb hypsochromically when compared with their pyrrolidinyl counterparts.In acid solution, the pyrrolidinyl dyes protonate almost exclusively at the β-azo nitrogen atom (azonium tautomer), whereas the analogous piperidino compounds protonate very largely at the terminal nitrogen atom (ammonium tautomer).These effects are related to differences in the conjugative capacity of the lone pair of electrons on the terminal nitrogen atom brought about by a change in size of the saturated heterocyclic ring.
