A convenient one-pot nanosynthesis of a C(sp2)–C(sp3)-linked 3D grid via an ‘A2 + B3’ approach

Ying Wei; Mengcheng Luo; Guangwei Zhang; Jiaqi Lei; Ling-Hai Xie; Wei Huang

doi:10.1039/C9OB00754G

A convenient one-pot nanosynthesis of a C(sp²)–C(sp³)-linked 3D grid via an ‘A₂ + B₃’ approach†

Ying Wei,

^a Mengcheng Luo,^a Guangwei Zhang,*^a Jiaqi Lei,^a Ling-Hai Xie

*^a and Wei Huang^ab

Author affiliations

* Corresponding authors

^a Centre for Molecular Systems and Organic Devices (CMSOD), Key Laboratory for Organic Electronics and Information Displays & Jiangsu Key Laboratory for Biosensors, Institute of Advanced Materials (IAM), Jiangsu National Synergetic Innovation Center for Advanced Materials (SICAM), Nanjing University of Posts & Telecommunications, 9 Wenyuan Road, Nanjing 210023, P.R. China
E-mail: iamlhxie@njupt.edu.cn, iamgwzhang@njupt.edu.cn

^b Shaanxi Institute of Flexible Electronics (SIFE), Northwestern Polytechnical University (NPU), 127 West Youyi Road, Xi'an 710072, Shaanxi, China

Abstract

Fluorene-based 3D-grid-FTPA was synthesised with a total yield of 55% via the one-pot formation of six C(sp²)–C(sp³) bonds through a BF₃·Et₂O-mediated Friedel–Crafts reaction of A₂-type bifluorene tertiary alcohol (BIOH) and two B₃-type triphenylamines. At the same time, Un-grid-FTPA (2.7%) and 2D-grid-FTPA (5.6%) were obtained as by-products from this synthesis method. In addition, the effect of stereoisomers of BIOH was evaluated to demonstrate that Rac-BIOH is a better A₂-type building block to prepare 3D-grid-FTPA in a relatively high yield. Furthermore, 3D-grid-FTPA showed excellent chemical, thermal, and photo-stabilities.

This article is part of the themed collection: Supramolecular chemistry in OBC

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Article information

DOI: https://doi.org/10.1039/C9OB00754G
Article type: Communication
Submitted: 02 avr. 2019
Accepted: 12 juin 2019
First published: 15 juin 2019

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Org. Biomol. Chem., 2019,17, 6574-6579

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A convenient one-pot nanosynthesis of a C(sp²)–C(sp³)-linked 3D grid via an ‘A₂ + B₃’ approach

Y. Wei, M. Luo, G. Zhang, J. Lei, L. Xie and W. Huang, Org. Biomol. Chem., 2019, 17, 6574 DOI: 10.1039/C9OB00754G

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Organic & Biomolecular Chemistry