New Thiolated Nitrophenylhydrazone Crystals for Nonlinear Optics

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We investigate new 4-nitophenylhydrazone crystals with thiolated electron donors for nonlinear optical applications. The methylthiolated (SM) electron donor and the biphenyl sulfane (SB) electron donor, which promotes a herringbone packing motif, are incorporated with an acentric nonlinear optical core, nitrophenylhydrazone (NPH), which promotes a lambda-shaped packing motif in the crystalline state. SM-NPH (4-(methylthio)benzaldehyde-4-nitrophenylhydrazone) crystals show head-to-tail hydrogen-bonded chains, which outweigh the usual lambda-shaped packing of the nitrophenylhydrazone group. SB-NPH crystals (4-(phenylthio)benzaldehyde-4-nitrophenylhydrazone) show simultaneous lambda-shaped packing, based on the hydrogen bonds of nitrophenylhydrazone with the nitro electron acceptor group, and the herringbone-shaped packing of biphenyl sulfane groups. Polar SM-NPH chains pack in a centrosymmetric crystal structure, while SB-NPH crystals exhibit a large macroscopic second-order nonlinearity resulting from an acentric molecular ordering of two rotational isomers. In addition, SB-NPH crystals undergo an irreversible phase transition before melting, with the second phase being also acentric with a strong second harmonic generation efficiency.
Publisher
AMER CHEMICAL SOC
Issue Date
2012-01
Language
English
Article Type
Article
Keywords

CONFIGURATIONALLY LOCKED POLYENE; SINGLE-CRYSTALS; STILBAZOLIUM DERIVATIVES; HYDRAZONE DERIVATIVES; ORGANIC SALTS; GROWTH; 4-NITROPHENYLHYDRAZONES; POLYMORPHS; PACKING

Citation

CRYSTAL GROWTH DESIGN, v.12, no.1, pp.313 - 319

ISSN
1528-7483
DOI
10.1021/cg201115s
URI
http://hdl.handle.net/10203/98061
Appears in Collection
CH-Journal Papers(저널논문)PH-Journal Papers(저널논문)
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