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

Supplementary files

Article information

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

Download Citation

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

Permissions

Request permissions

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

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Organic & Biomolecular Chemistry