Pyrrole-Based Hydrazone Organic Nonlinear Optical Crystals and Their Polymorphs

被引:44
|
作者
Kwon, O-Pil [1 ,2 ]
Jazbinsek, Mojca [2 ]
Yun, Hoseop [3 ,4 ]
Seo, Jung-In [5 ,6 ]
Kim, Eun-Mi [1 ]
Lee, Yoon-Sup [5 ,6 ]
Guenter, Peter [2 ]
机构
[1] Ajou Univ, Dept Mol Sci & Technol, Suwon 443749, South Korea
[2] ETH, Nonlinear Opt Lab, CH-8093 Zurich, Switzerland
[3] Ajou Univ, Div Energy Syst Res, Suwon 443749, South Korea
[4] Ajou Univ, Dept Chem, Suwon 443749, South Korea
[5] Korea Adv Inst Sci & Technol, Dept Chem, Taejon 305701, South Korea
[6] Korea Adv Inst Sci & Technol, Sch Mol Sci BK 21, Taejon 305701, South Korea
基金
瑞士国家科学基金会;
关键词
D O I
10.1021/cg800218u
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A series of new organic nonlinear optical nitrophenylhydrazone crystals based on pyrrole with various substituents (X: -H, -CH3, -CF3) on the hydrazone group (-CX = N-NH-) has been synthesized and their polymorphs have been investigated. The chromophore 2-((2-(4-nitrophenyl)hydrazono)methyl)-1H-pyrrole (HNPH) exhibits two polymorphs with large macroscopic nonlinearity, with a powder second harmonic generation activity of 420 times and 210 times that of urea at 1.9 mu m for the anisotropic polar HNPH-I with P-n space group and the isotropic nonpolar HNPH-II polymorph with P2(1)2(1)2(1) space group, respectively. The microscopic and macroscopic nonlinearities in the crystallographic system have been analyzed theoretically using finite field calculations.
引用
收藏
页码:4021 / 4025
页数:5
相关论文
共 50 条
  • [31] MOLECULAR-WEIGHT DETERMINATION OF PYRROLE-BASED POLYMERS
    NAZZAL, A
    STREET, GB
    JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1984, (02) : 83 - 84
  • [32] ELECTRONIC-STRUCTURE OF PYRROLE-BASED CONDUCTING POLYMERS
    FINK, J
    SCHEERER, B
    WERNET, W
    MONKENBUSCH, M
    WEGNER, G
    FREUND, HJ
    GONSKA, H
    SYNTHETIC METALS, 1987, 18 (1-3) : 71 - 76
  • [33] Luminescent properties of pyrrole-based heterocyclic conjugated polymers
    Abe, S
    Nagasaki, Y
    Kijima, M
    SYNTHETIC METALS, 2003, 135 (1-3) : 123 - 124
  • [34] Synthesis and characterization of some pyrrole-based aldimine monomers
    Grigoras, M
    Stoica, G
    Cianga, I
    Simionescu, CI
    REVUE ROUMAINE DE CHIMIE, 1997, 42 (10) : 993 - 998
  • [35] Second-order nonlinear optical organic crystals based on a "click" compound
    Zheng, Yongshen
    Guan, Junjie
    Cheng, Puxin
    Han, Wenqing
    Xu, Jialiang
    Bu, Xian-He
    JOURNAL OF MATERIALS CHEMISTRY C, 2023, 11 (20) : 6724 - 6729
  • [36] Organic nonlinear optical crystals based on configurationally locked polyene for melt growth
    Kwon, O-Pil
    Ruiz, Blanca
    Choubey, Ashutosh
    Mutter, Lukas
    Schneider, Arno
    Jazbinsek, Mojca
    Gramlich, Volker
    Guenter, Peter
    CHEMISTRY OF MATERIALS, 2006, 18 (17) : 4049 - 4054
  • [37] Acentric Nonlinear Optical 2,4-Dihydroxyl Hydrazone Isomorphic Crystals with Large Linear, Nonlinear Optical Susceptibilities and Hyperpolarizability
    Reshak, A. H.
    Kamarudin, H.
    Auluck, S.
    JOURNAL OF PHYSICAL CHEMISTRY B, 2012, 116 (15): : 4677 - 4683
  • [38] Low band-gap pyrrole-based conducting polymers
    Berlin, A
    Canavesi, A
    Pagani, G
    Schiavon, G
    Zecchin, S
    Zotti, G
    SYNTHETIC METALS, 1997, 84 (1-3) : 451 - 452
  • [39] First hyperpolarizability orientation in asymmetric pyrrole-based polyene chromophores
    Kwon, O-Pil
    Jazbinsek, Mojca
    Seo, Jung-In
    Kim, Pil-Joo
    Choi, Eun-Young
    Lee, Yoon Sup
    Guenter, Peter
    DYES AND PIGMENTS, 2010, 85 (03) : 162 - 170
  • [40] Redox chemistry of pyrrole-based ligands in transition metal complexes
    Lincoln, Kimberly
    Gautam, Ritika
    Tomat, Elisa
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2016, 251