Extended π‐Conjugated Pyrene Derivatives: Structural, Photophysical and Electrochemical Properties. Issue 9 (21st June 2016)

• Record Type: Journal Article
• Authors: Feng , Xing; Seto, Nobuyuki; Wang, Chuan‐Zeng; Matsumoto, Taisuke; Tanaka, Junji; Wei, Xian‐Fu; Elsegood, Mark R. J.; Horsburgh, Lynne; Redshaw, Carl; Yamato, Takehiko
• Is Part Of: ChemistrySelect. Volume 1:Issue 9(2016)
• Page Start: 1926
• Page End: 1932
• Publication Date: 2016-06-21
• Subjects: Pyrenes -- Intramolecular charge-transfer -- Single crystals -- Luminescence material -- Structure-property relationship; Chemistry -- Periodicals; 540.5
• DOI: 10.1002/slct.201600598
• Languages: English
• ISSNs: 2365-6549

Abstract

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 in2 d or2 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 compounds2 d and2 f possess strong CT characteristics. Abstract : A series of high‐efficiency luminescent material, namely 1, 3‐di(arylethynyl)‐7‐ tert ‐butylpyrenes, which were synthesized by a palladium‐catalyzed Sonogashira coupling reaction. The detailed photophysical and electrochemical properties of titled compounds have been thoroughly investigated by experimental and theoretical.