Synthesis and Characterization of Electro-optic Materials Based on Intermolecular Lateral Hydrogen Bonding†

doi:10.7503/cjcu20150402

Abstract

Abstract:

A new series of azobenzene nonlinear optical(NLO) chromophores was prepared by diazo coupling and esterification reactions, and the “gest-host” and “supramolecular” NLO materials were also prepared by doping or intermolecular lateral hydrogen bonding interaction. The chemical structures of these chromophores were characterized. The intermolecular lateral hydrogen bonding interaction in these chromophores was confirmed by ¹H NMR. The UV-Vis spectra of these NLO materials showed that the chromophore loading, poling efficiency and alignment stability could be greatly improved by the intermolecular lateral hydrogen bonding interaction. The electro-optic(E-O) activities of these materials were also studied. Compared with “gest-host” type, the “supramolecular” type NLO materials based on the intermolecular lateral hydrogen bonding interaction had larger E-O coefficients.

Key words: Second-order nonlinear optics property, Lateral hydrogen bonding, Supramolecule type electrooptic material, Poling efficiency, Azobenzene chromophore

CLC Number:

O631

TrendMD:

ZHANG Qingzhong, ZHANG Junmei, LIU Yuping, REN Xiao, HUANG Wei. Synthesis and Characterization of Electro-optic Materials Based on Intermolecular Lateral Hydrogen Bonding^†[J]. Chem. J. Chinese Universities, 2015, 36(10): 2053.

Figures/Tables 9

Synthesis routes of electro-optic chromophores NLO1—NLO4

Fig.1 FTIR spectra of NLO2(a) and NLO4(b)

Fig.2 1H NMR spectra of NLO2(a) and NLO4(b) in DMSO-d6

Fig.3 1H NMR spectra of NLO3 at different concentrations in CDCl3^Concentration of NLO3/(mg·mL-1): a. 3; b. 15; c. 30.

Table 1 Poling conditions of electro-optic films for 30 min

Sample	Temperature/℃	Voltage/V	Current/μA
NLO1/APC(S1)	100	4100	3
NLO2/APC(S2)	100	3950	4
NLO3(S3)	95	3900	3
NLO4(S4)	100	3750	3

Table 2 Stability of order parameter of electro-optic films*

Sample	Φ₁	Φ₂	Φ₂/Φ₁(%)
NLO1/APC(S1)	0.14	0.11	78.6
NLO2/APC(S2)	0.13	0.10	76.9
NLO3(S3)	0.49	0.43	87.8
NLO4(S4)	0.55	0.53	94.6

Fig.4 UV-Vis spectra of films before(a) and after poling(b) and long time after poling(c)^(A) S1; (B) S2; (C) S3; (D) S4.

Fig.5 Polarization orientation's schematic diagram of electro-optic materials based on the lateral hydrogen bonding

Table 3 Electro-optic coefficient of films

Sample	10^-20N of dye^a/cm^-3	/(pm·V^-1)
NLO1/APC(S1)	2.4	11
NLO2/APC(S2)	2.3	10
NLO3(S3)	10.5	31
NLO4(S4)	8.7	34

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