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

1 Citation (Scopus)

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

Fingerprint

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.
@article{3767a46e8af54a8994500607c980554e,
title = "Extended π-Conjugated Pyrene Derivatives: Structural, Photophysical and Electrochemical Properties",
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.",
author = "Xing Feng and Nobuyuki Seto and Wang, {Chuan Zeng} and Taisuke Matsumoto and Junji Tanaka and Wei, {Xian Fu} and Elsegood, {Mark R.J.} and Lynne Horsburgh and Carl Redshaw and Takehiko Yamato",
year = "2016",
month = "1",
day = "1",
doi = "10.1002/slct.201600598",
language = "English",
volume = "1",
pages = "1926--1932",
journal = "ChemistrySelect",
issn = "2365-6549",
publisher = "Wiley-Blackwell Publishing Ltd",
number = "9",

}

TY - JOUR

T1 - Extended π-Conjugated Pyrene Derivatives

T2 - Structural, Photophysical and Electrochemical Properties

AU - Feng, Xing

AU - Seto, Nobuyuki

AU - Wang, Chuan Zeng

AU - Matsumoto, Taisuke

AU - Tanaka, Junji

AU - Wei, Xian Fu

AU - Elsegood, Mark R.J.

AU - Horsburgh, Lynne

AU - Redshaw, Carl

AU - Yamato, Takehiko

PY - 2016/1/1

Y1 - 2016/1/1

N2 - 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.

AB - 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.

UR - http://www.scopus.com/inward/record.url?scp=85041953275&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85041953275&partnerID=8YFLogxK

U2 - 10.1002/slct.201600598

DO - 10.1002/slct.201600598

M3 - Article

VL - 1

SP - 1926

EP - 1932

JO - ChemistrySelect

JF - ChemistrySelect

SN - 2365-6549

IS - 9

ER -