Journal of Materials Chemistry p. 2101 - 2106 (2007)
Update date:2022-08-04
Topics:
Zhu, Yun-Ji
Qin, An-Jun
Fu, Li-Min
Ai, Xi-Cheng
Guo, Zhi-Xin
Zhang, Jian-Ping
Ye, Cheng
We have synthesized three new 1,3-diazaazulene derivatives, namely, 2-(4′-N,N-dimethylaminophenyl)-6-nitro-1,3-diazaazulene (18, DMAPNA), 2-(4′-aminophenyl)-6-nitro-1,3-diazaazulene (19, APNA) and 2-[4′-N-(2-hydroxyethyl)aminophenyl]-6-nitro-1,3-diazaazulene (20, HEAPNA), each of them contains an amino substitute as the electron donor (D), 2-phenyl-1,3-diazaazulene as the π-conjugated bridge and a nitro as the electron acceptor (A). Our theoretical results have predicted that these D-π-A type chromophores possess low ground-state dipole moment (μg) and large first-order hyperpolarizability (β), which may facilitate a low degree of aggregation for the chromophores dispersed in a polymeric matrix as well as a large nonlinear optical (NLO) response. The expected NLO performance has been confirmed by the experimental β and μg values, e.g., for 18, 407.8 × 10-30 esu and 4.7 D, respectively. The origins of large β and low μg are explained in terms of a two-state quantum model. The DMAPNA (18)-doped and poled polymethylmethacrylate film exhibits a large second harmonic generation (SHG) coefficient of d33 = 10.9 pm V-1 with excellent thermal stability (above 70% of the maximal SHG coefficient remains at ~100 °C). The Royal Society of Chemistry.
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