Extended π-Conjugated Pyrene Derivatives: Structural, Photophysical and Electrochemical Properties

Xing Feng, Nobuyuki Seto, Chuan Zeng Wang, Taisuke Matsumoto, Junji Tanaka, Xian Fu Wei, Mark R.J. Elsegood, Lynne Horsburgh, Carl Redshaw, Takehiko Yamato

Research output: Contribution to journalArticle

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Abstract

This article presents a set of extended π-conjugated pyrene derivatives, namely 1,3-di(arylethynyl)-7-tert-butylpyrenes, which were synthesized by a Pd-catalyzed Sonogashira coupling reaction of 1,3-dibromo-7-tert-butylpyrenes with the corresponding arylethynyl group in good yields. Despite the presence of the tert-butyl group located at the 7-position of pyrene, X-ray crystallographic analyses show that the planarity of the Y-shaped molecules still exhibits strong face-to-face π-π stacking in the solid state; all of the compounds exhibit blue or green emission with high quantum yields (QYs) in dichloromethane. DFT calculations and electrochemistry revealed that this category of compound possesses hole-transporting characteristics. In addition, with strong electron-donating (-N(CH3)2) or electron-withdrawing (-CHO) groups in 2 d or 2 f, these molecules displayed efficient intramolecular charge-transfer (ICT) emissions with solvatochromic shifts from blue to yellow (green) on increasing the solvent polarity. Furthermore, the compounds 2 d and 2 f possess strong CT characteristics.

Original languageEnglish
Pages (from-to)1926-1932
Number of pages7
JournalChemistrySelect
Volume1
Issue number9
DOIs
Publication statusPublished - Jan 1 2016

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Electrochemical properties
Structural properties
Derivatives
Molecules
Electrons
Methylene Chloride
Electrochemistry
Quantum yield
Discrete Fourier transforms
Charge transfer
X rays
pyrene
Green Or

All Science Journal Classification (ASJC) codes

  • Chemistry(all)

Cite this

Extended π-Conjugated Pyrene Derivatives : Structural, Photophysical and Electrochemical Properties. / Feng, Xing; Seto, Nobuyuki; Wang, Chuan Zeng; Matsumoto, Taisuke; Tanaka, Junji; Wei, Xian Fu; Elsegood, Mark R.J.; Horsburgh, Lynne; Redshaw, Carl; Yamato, Takehiko.

In: ChemistrySelect, Vol. 1, No. 9, 01.01.2016, p. 1926-1932.

Research output: Contribution to journalArticle

Feng, X, Seto, N, Wang, CZ, Matsumoto, T, Tanaka, J, Wei, XF, Elsegood, MRJ, Horsburgh, L, Redshaw, C & Yamato, T 2016, 'Extended π-Conjugated Pyrene Derivatives: Structural, Photophysical and Electrochemical Properties', ChemistrySelect, vol. 1, no. 9, pp. 1926-1932. https://doi.org/10.1002/slct.201600598
Feng, Xing ; Seto, Nobuyuki ; Wang, Chuan Zeng ; Matsumoto, Taisuke ; Tanaka, Junji ; Wei, Xian Fu ; Elsegood, Mark R.J. ; Horsburgh, Lynne ; Redshaw, Carl ; Yamato, Takehiko. / Extended π-Conjugated Pyrene Derivatives : Structural, Photophysical and Electrochemical Properties. In: ChemistrySelect. 2016 ; Vol. 1, No. 9. pp. 1926-1932.
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