Striking effect of intra- versus intermolecular hydrogen bonding on zwitterions: Physical and electronic properties

Yonghao Zheng; Mao Sheng Miao; Yuan Zhang; Thuc Quyen Nguyen; Fred Wudl

doi:10.1021/ja506803y

Striking effect of intra- versus intermolecular hydrogen bonding on zwitterions: Physical and electronic properties

Yonghao Zheng
, Mao Sheng Miao
, Yuan Zhang
, Thuc Quyen Nguyen
, Fred Wudl^*

^*Corresponding author for this work

University of California at Santa Barbara
California NanoSystems Institute
China Academy of Engineering Physics

Research output: Contribution to journal › Article › peer-review

14 Scopus citations

Abstract

We report the synthesis, characterization, and application of novel zwitterions. The zwitterionic structures consist of a positively charged cyanine and negatively charged dienolate moieties, confirmed by experimental observations and theoretical calculations. Single crystal X-ray studies revealed that BIT-(NPh)₂ is a coplanar molecule that forms 1-D chains via π-π interactions. In contrast, BIT-(NHexyl)₂ is a twisted molecule with a dihedral angle of 78° between the charged planes. In charge transport studies, thin films of the flat zwitterion show semiconducting properties, with a hole mobility of 2.1 × 10^-4 cm² V^-1 s^-1 while the twisted zwitterion is a high resistivity insulator.

Original language	English
Pages (from-to)	11614-11617
Number of pages	4
Journal	Journal of the American Chemical Society
Volume	136
Issue number	33
DOIs	https://doi.org/10.1021/ja506803y
State	Published - 20 Aug 2014
Externally published	Yes

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title = "Striking effect of intra- versus intermolecular hydrogen bonding on zwitterions: Physical and electronic properties",

abstract = "We report the synthesis, characterization, and application of novel zwitterions. The zwitterionic structures consist of a positively charged cyanine and negatively charged dienolate moieties, confirmed by experimental observations and theoretical calculations. Single crystal X-ray studies revealed that BIT-(NPh)2 is a coplanar molecule that forms 1-D chains via π-π interactions. In contrast, BIT-(NHexyl)2 is a twisted molecule with a dihedral angle of 78° between the charged planes. In charge transport studies, thin films of the flat zwitterion show semiconducting properties, with a hole mobility of 2.1 × 10-4 cm2 V-1 s-1 while the twisted zwitterion is a high resistivity insulator.",

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T2 - Physical and electronic properties

AU - Zheng, Yonghao

AU - Miao, Mao Sheng

AU - Zhang, Yuan

AU - Nguyen, Thuc Quyen

AU - Wudl, Fred

PY - 2014/8/20

Y1 - 2014/8/20

N2 - We report the synthesis, characterization, and application of novel zwitterions. The zwitterionic structures consist of a positively charged cyanine and negatively charged dienolate moieties, confirmed by experimental observations and theoretical calculations. Single crystal X-ray studies revealed that BIT-(NPh)2 is a coplanar molecule that forms 1-D chains via π-π interactions. In contrast, BIT-(NHexyl)2 is a twisted molecule with a dihedral angle of 78° between the charged planes. In charge transport studies, thin films of the flat zwitterion show semiconducting properties, with a hole mobility of 2.1 × 10-4 cm2 V-1 s-1 while the twisted zwitterion is a high resistivity insulator.

AB - We report the synthesis, characterization, and application of novel zwitterions. The zwitterionic structures consist of a positively charged cyanine and negatively charged dienolate moieties, confirmed by experimental observations and theoretical calculations. Single crystal X-ray studies revealed that BIT-(NPh)2 is a coplanar molecule that forms 1-D chains via π-π interactions. In contrast, BIT-(NHexyl)2 is a twisted molecule with a dihedral angle of 78° between the charged planes. In charge transport studies, thin films of the flat zwitterion show semiconducting properties, with a hole mobility of 2.1 × 10-4 cm2 V-1 s-1 while the twisted zwitterion is a high resistivity insulator.

UR - https://www.scopus.com/pages/publications/84906342391

U2 - 10.1021/ja506803y

DO - 10.1021/ja506803y

M3 - 文章

AN - SCOPUS:84906342391

SN - 0002-7863

VL - 136

SP - 11614

EP - 11617

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

IS - 33

ER -

Striking effect of intra- versus intermolecular hydrogen bonding on zwitterions: Physical and electronic properties

Abstract

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