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

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 intram...

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Bibliographic Details
Published in:Tetrahedron 2013-07, Vol.69 (30), p.6317-6322
Main Authors: Yang, Yang, Zhao, Jian-Feng, Liu, Ran-Ran, Li, Jie-Wei, Yi, Ming-Dong, Xie, Guo-Hua, Xie, Ling-Hai, Chang, Yong-Zheng, Yin, Cheng-Rong, Zhou, Xin-Hui, Zhao, Yi, Qian, Yan, Huang, Wei
Format: Article
Language:English
Subjects:
Diarylfluorenes
Friedel–Crafts reaction
Non-covalent bond
Organic complex
π-Stacks
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Summary: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/m2, 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. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2013.02.090