ICCAS OpenIR
Synthesis and properties of novel second-order NLO chromophores containing pyrrole as an auxiliary electron donor
Ma, Xiaohua1; Liang, Ran2; Yang, Fan2; Zhao, Zhenhua1; Zhang, Aixin1; Song, Naiheng1; Zhou, Qifeng1; Zhang, Jianping2
2008
Source PublicationJOURNAL OF MATERIALS CHEMISTRY
ISSN0959-9428
Volume18Issue:15Pages:1756-1764
AbstractA novel series of second-order NLO chromophores containing pyrrole as an auxiliary electron donor was synthesized via Knoevenagel reactions between 5-aminated N-methylpyrrole-2-carbaldehydes and different electron-accepting groups, i.e., malononitrile, picolinium tosylate and 2-dicyanomethylene-3-cyano-4,5,5-trimethyl-2,5-dihydrofuran (TCF). Their corresponding NLO chromophores containing thiophene in the place of pyrrole were also prepared for comparison. The resulting NLO chromophores showed good solubility in common organic solvents such as CHCl3, THF and DMF, except for TTCF containing thiophene and TCF, which is soluble in polar aprotic solvents but poorly soluble in less polar solvents. NMR studies of these chromophores showed that, in comparison with thiophene rings in the same type of NLO chromophores, pyrrole rings had higher electron density, as evidenced by the up-field chemical shifts of pyrrole protons. TGA investigations showed good thermal stability of these chromophores in nitrogen with the onset weight loss temperatures in the range of 203 to 296 degrees C. Positive solvatochromism of 10-44 nm from dioxane to chloroform were found for these chromophores, and moderate to very large molecular static hyperpolarizabilities (beta(0)) of 57-1490 x 10(-30) esu were revealed by hyper-Rayleigh scattering measurements. For chemical bonding to polymer chains, hydroxyl-containing NLO chromophores were also prepared and characterized for their linear and nonlinear optical properties.
DOI10.1039/b720023d
Indexed BySCI
Language英语
WOS IDWOS:000254648100006
PublisherROYAL SOC CHEMISTRY
Citation statistics
Cited Times:32[WOS]   [WOS Record]     [Related Records in WOS]
Document Type期刊论文
Identifierhttp://ir.iccas.ac.cn/handle/121111/63010
Collection中国科学院化学研究所
Corresponding AuthorSong, Naiheng
Affiliation1.Peking Univ, Coll Chem & Mol Engn, Dept Polymer Sci & Engn,Beijing Natl Lab Mol Sci, Key Lab Polymer Chem & Phys,Minist Educ, Beijing 100871, Peoples R China
2.Renmin Univ China, Dept Chem, Beijing 100872, Peoples R China
Recommended Citation
GB/T 7714
Ma, Xiaohua,Liang, Ran,Yang, Fan,et al. Synthesis and properties of novel second-order NLO chromophores containing pyrrole as an auxiliary electron donor[J]. JOURNAL OF MATERIALS CHEMISTRY,2008,18(15):1756-1764.
APA Ma, Xiaohua.,Liang, Ran.,Yang, Fan.,Zhao, Zhenhua.,Zhang, Aixin.,...&Zhang, Jianping.(2008).Synthesis and properties of novel second-order NLO chromophores containing pyrrole as an auxiliary electron donor.JOURNAL OF MATERIALS CHEMISTRY,18(15),1756-1764.
MLA Ma, Xiaohua,et al."Synthesis and properties of novel second-order NLO chromophores containing pyrrole as an auxiliary electron donor".JOURNAL OF MATERIALS CHEMISTRY 18.15(2008):1756-1764.
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