Diarylfluorenes-based π-stacked molecules: Synthesis, X-ray crystallography, and supramolecular light-emitting devices

Yang Yang; Jian Feng Zhao; Ran Ran Liu; Jie Wei Li; Ming Dong Yi; Guo Hua Xie; Ling Hai Xie; Yong Zheng Chang; Cheng Rong Yin; Xin Hui Zhou; Yi Zhao; Yan Qian; Wei Huang

doi:10.1016/j.tet.2013.02.090

Diarylfluorenes-based π-stacked molecules: Synthesis, X-ray crystallography, and supramolecular light-emitting devices

Yang Yang, Jian Feng Zhao, Ran Ran Liu, Jie Wei Li, Ming Dong Yi, Guo Hua Xie, Ling Hai Xie, Yong Zheng Chang, Cheng Rong Yin, Xin Hui Zhou, Yi Zhao, Yan Qian, Wei Huang

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

14 Scopus citations

Abstract

A series of intramolecular π-stacked molecules as new-concept supramolecular organic semiconductors have been designed by means of the ortho-substituted steric hindrance of diarylfluorenes and facile synthesized via the key step of BF₃·Et₂O-mediated Friedel-Crafts reaction of carbinols. Their intramolecular π-π stacking interactions were corroborated by the X-ray crystallography, NMR, as well as theoretical simulation. The supramolecular organic light-emitting devices exhibited an anomalous electroluminescence with a maximum luminance of ca. 1282 cd/m ², a luminous efficiency of 0.24 cd/A, and a turn-on voltage of 9 V. The π-stacked semiconductors are potential models of supramolecular semiconductors and optoelectronics.

Original language	English
Pages (from-to)	6317-6322
Number of pages	6
Journal	Tetrahedron
Volume	69
Issue number	30
DOIs	https://doi.org/10.1016/j.tet.2013.02.090
State	Published - 29 Jul 2013
Externally published	Yes

Keywords

π-Stacks
Diarylfluorenes
Friedel-Crafts reaction
Non-covalent bond
Organic complex

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10.1016/j.tet.2013.02.090

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title = "Diarylfluorenes-based π-stacked molecules: Synthesis, X-ray crystallography, and supramolecular light-emitting devices",

abstract = "A series of intramolecular π-stacked molecules as new-concept supramolecular organic semiconductors have been designed by means of the ortho-substituted steric hindrance of diarylfluorenes and facile synthesized via the key step of BF3·Et2O-mediated Friedel-Crafts reaction of carbinols. Their intramolecular π-π stacking interactions were corroborated by the X-ray crystallography, NMR, as well as theoretical simulation. The supramolecular organic light-emitting devices exhibited an anomalous electroluminescence with a maximum luminance of ca. 1282 cd/m 2, a luminous efficiency of 0.24 cd/A, and a turn-on voltage of 9 V. The π-stacked semiconductors are potential models of supramolecular semiconductors and optoelectronics.",

keywords = "π-Stacks, Diarylfluorenes, Friedel-Crafts reaction, Non-covalent bond, Organic complex",

author = "Yang Yang and Zhao, {Jian Feng} and Liu, {Ran Ran} and Li, {Jie Wei} and Yi, {Ming Dong} and Xie, {Guo Hua} and Xie, {Ling Hai} and Chang, {Yong Zheng} and Yin, {Cheng Rong} and Zhou, {Xin Hui} and Yi Zhao and Yan Qian and Wei Huang",

year = "2013",

month = jul,

day = "29",

doi = "10.1016/j.tet.2013.02.090",

language = "英语",

volume = "69",

pages = "6317--6322",

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TY - JOUR

T1 - Diarylfluorenes-based π-stacked molecules

T2 - Synthesis, X-ray crystallography, and supramolecular light-emitting devices

AU - Yang, Yang

AU - Zhao, Jian Feng

AU - Liu, Ran Ran

AU - Li, Jie Wei

AU - Yi, Ming Dong

AU - Xie, Guo Hua

AU - Xie, Ling Hai

AU - Chang, Yong Zheng

AU - Yin, Cheng Rong

AU - Zhou, Xin Hui

AU - Zhao, Yi

AU - Qian, Yan

AU - Huang, Wei

PY - 2013/7/29

Y1 - 2013/7/29

N2 - A series of intramolecular π-stacked molecules as new-concept supramolecular organic semiconductors have been designed by means of the ortho-substituted steric hindrance of diarylfluorenes and facile synthesized via the key step of BF3·Et2O-mediated Friedel-Crafts reaction of carbinols. Their intramolecular π-π stacking interactions were corroborated by the X-ray crystallography, NMR, as well as theoretical simulation. The supramolecular organic light-emitting devices exhibited an anomalous electroluminescence with a maximum luminance of ca. 1282 cd/m 2, a luminous efficiency of 0.24 cd/A, and a turn-on voltage of 9 V. The π-stacked semiconductors are potential models of supramolecular semiconductors and optoelectronics.

AB - A series of intramolecular π-stacked molecules as new-concept supramolecular organic semiconductors have been designed by means of the ortho-substituted steric hindrance of diarylfluorenes and facile synthesized via the key step of BF3·Et2O-mediated Friedel-Crafts reaction of carbinols. Their intramolecular π-π stacking interactions were corroborated by the X-ray crystallography, NMR, as well as theoretical simulation. The supramolecular organic light-emitting devices exhibited an anomalous electroluminescence with a maximum luminance of ca. 1282 cd/m 2, a luminous efficiency of 0.24 cd/A, and a turn-on voltage of 9 V. The π-stacked semiconductors are potential models of supramolecular semiconductors and optoelectronics.

KW - π-Stacks

KW - Diarylfluorenes

KW - Friedel-Crafts reaction

KW - Non-covalent bond

KW - Organic complex

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U2 - 10.1016/j.tet.2013.02.090

DO - 10.1016/j.tet.2013.02.090

M3 - 文章

AN - SCOPUS:84878932607

SN - 0040-4020

VL - 69

SP - 6317

EP - 6322

JO - Tetrahedron

JF - Tetrahedron

IS - 30

ER -

Diarylfluorenes-based π-stacked molecules: Synthesis, X-ray crystallography, and supramolecular light-emitting devices

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Keywords

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