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Liquid Crystals Volume 38, 2011 - Issue 6
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Original Articles

Direct evidence for the effect of lateral hydrogen bonding on the smectic phase

Haitao Wang State Key Laboratory of Theoretical and Computational Chemistry, Institute of Theoretical Chemistry, Jilin University, Changchun, China; Key Laboratory of Automobile Materials (MOE) & College of Materials Science and Engineering, Jilin University, Changchun, China
,
Binglian Bai College of Physics, Jilin University, Changchun, China
,
Fu-Quan Bai State Key Laboratory of Theoretical and Computational Chemistry, Institute of Theoretical Chemistry, Jilin University, Changchun, China
,
Dongmei Pang Key Laboratory of Automobile Materials (MOE) & College of Materials Science and Engineering, Jilin University, Changchun, China
,
Xia Ran Key Laboratory of Automobile Materials (MOE) & College of Materials Science and Engineering, Jilin University, Changchun, China
,
Chengxiao Zhao Key Laboratory of Automobile Materials (MOE) & College of Materials Science and Engineering, Jilin University, Changchun, China
,
Hong-Xing Zhang State Key Laboratory of Theoretical and Computational Chemistry, Institute of Theoretical Chemistry, Jilin University, Changchun, ChinaCorrespondence[email protected]
&
Min Li Key Laboratory of Automobile Materials (MOE) & College of Materials Science and Engineering, Jilin University, Changchun, China
 show all
Pages 767-774 | Received 12 Feb 2011, Accepted 16 Mar 2011, Published online: 14 Jun 2011
 
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Abstract

In order to reduce the number of hydrogen bonds in biamide derivatives, one amide group in N-(4-cetyloxybenzoyl)-N'-(4'-nitrobenzoyl) hydrazine (C16-NO2) was replaced by a Schiff base group, forming N-(4-cetyloxybenzoyl)-N'-(4'-nitrobenzylidene) hydrazine (C16-Sch). Computational study on the molecular structure at B3LYP/6–311+G** level revealed that the molecular geometry of C16-NO2 could be well retained by C16-Sch. In addition, C16-Sch exhibited the same mesophase structure (SmA1) as C16-NO2, and the hydrogen bonding was demonstrated to be still interacting in the mesophase. However, compared to C16-NO2, the mesophase stability of C16-Sch is dramatically decreased by the reduction of the number of hydrogen bonds, providing direct evidence that intermolecular hydrogen bonding plays an important role in stabilising the smectic phase.

Acknowledgements

This work was supported by the National Science Foundation of China (50873044, 51073071, 20973076 and 21003057) and Jilin University (200903014).

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