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
N1 - Funding Information:
This work was performed under the Cooperative Research Program of “Network Joint Research Center for Materials and Devices (Institute for Materials Chemistry and Engineering, Kyushu University)”. We also would like to thank the EPSRC (overseas travel grant to C.R.), The Scientific Research Foundation for the Returned Overseas Chinese Scholars, State Education Ministry, Fund Program for the Scientific Activities of Selected Returned Overseas Professionals of Beijing and The Scientific Research Common Program of Beijing Municipal Commission of Education for financial support (KM201510015003).
Publisher Copyright:
© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
PY - 2016/6/16
Y1 - 2016/6/16
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
AN - SCOPUS:85041953275
SN - 2365-6549
VL - 1
SP - 1926
EP - 1932
JO - ChemistrySelect
JF - ChemistrySelect
IS - 9
ER -