Issue 11, 2012
From the journal:

Organic & Biomolecular Chemistry

Highly emissive hand-shaped π-conjugated alkynylpyrenes: Synthesis, structures, and photophysical properties†

Jian-Yong Hu,*ab   Xin-Long Ni,a   Xing Feng,a   Masanao Era,a   Mark R. J. Elsegood,c   Simon J. Teatd  and  Takehiko Yamato*a  

* Corresponding authors

a Department of Applied Chemistry, Faculty of Science and Engineering, Saga University, Honjo machi 1, Saga-shi, Saga, Japan
E-mail: yamatot@cc.saga-u.ac.jp
Fax: +81-952-288548

b Department of Organic Device Engineering, Yamagata University, Yonezawa, Yamagata, Japan
E-mail: hujianyong@yz.yamagata-u.ac.jp
Fax: +81-238-263412

c Chemistry Department, Loughborough University, Loughborough, Leicestershire, UK

d Advanced Light Source, Berkeley Lab., 1 Cyclotron Road, Berkeley, CA, USA

Abstract

Three alkynyl-functionalised, hand-shaped, highly fluorescent and stable emitters, namely, 2-tert-butyl-4,5,7,9,10-pentakis(p-R-phenylethynyl)pyrenes have been successfully synthesized via a Pd/Cu-catalysed Sonogashira cross-coupling reaction. The chemical structures of the alkynylpyrenes were fully characterized by their 1H/13C NMR spectra, mass spectroscopy and elemental analysis. Synchrotron single-crystal X-ray analysis revealed that there is a 1-D, slipped, face-to-face motif with off-set, head-to-tail stacked columns, which are clearly influenced by the single, bulky, tert-butyl group in the pyrene ring at the 2-position. Detailed studies on the photophysical properties in both solutions and thin films strongly indicate that they might be promising candidates for optoelectronic applications, such as organic light-emitting devices (OLEDs) or as models for investigating the fluorescent structure–property relationship of the alkynyl-functionalised pyrene derivatives.

Graphical abstract: Highly emissive hand-shaped π-conjugated alkynylpyrenes: Synthesis, structures, and photophysical properties

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Article information

DOI
https://doi.org/10.1039/C2OB06865F
Article type
Paper
Submitted
04 Nov 2011
Accepted
21 Dec 2011
First published
22 Dec 2011

Org. Biomol. Chem., 2012,10, 2255-2262

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Highly emissive hand-shaped π-conjugated alkynylpyrenes: Synthesis, structures, and photophysical properties

J. Hu, X. Ni, X. Feng, M. Era, M. R. J. Elsegood, S. J. Teat and T. Yamato, Org. Biomol. Chem., 2012, 10, 2255 DOI: 10.1039/C2OB06865F

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