Regioselective Substitution at the 1,3-and 6,8-Positions of Pyrene for the Construction of Small Dipolar Molecules

被引:38
作者
Feng, Xing [1 ,2 ]
Tomiyasu, Hirotsugu [2 ]
Hu, Jian-Yong [3 ]
Wei, Xianfu [1 ]
Redshaw, Carl [4 ]
Elsegood, Mark R. J. [5 ]
Horsburgh, Lynne [5 ]
Teat, Simon J. [6 ]
Yamato, Takehiko [2 ]
机构
[1] Beijing Inst Graph Commun, Beijing 102600, Peoples R China
[2] Saga Univ, Fac Sci & Engn, Dept Appl Chem, Saga 8408502, Japan
[3] Shannxi Normal Univ, Sch Mat Sci & Engn, Xian 710062, Shannxi, Peoples R China
[4] Univ Hull, Dept Chem, Kingston Upon Hull HU6 7RX, N Humberside, England
[5] Univ Loughborough, Dept Chem, Loughborough LE11 3TU, Leics, England
[6] Berkeley Natl Lab, Adv Light Source, Berkeley, CA 94720 USA
基金
英国工程与自然科学研究理事会;
关键词
INTRAMOLECULAR-CHARGE-TRANSFER; PHOTOPHYSICAL PROPERTIES; ELECTRON-DONOR; DESIGN;
D O I
10.1021/acs.joc.5b02128
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
This article presents a novel asymmetrical functionalization strategy for the construction of dipolar molecules via efficient regioselective functionalization along the Z-axis of pyrene at both the 1,3- and 6,8-positions. Three asymmetrically substituted 1,3-diphenyl-6,8-R-disubsituted pyrenes were fully characterized by X-ray crystallography, photophysical properties, electrochemistry, and density functional theory calculations.
引用
收藏
页码:10973 / 10978
页数:6
相关论文
共 35 条
[1]   Dithienogermole As a Fused Electron Donor in Bulk Heterojunction Solar Cells [J].
Amb, Chad M. ;
Chen, Song ;
Graham, Kenneth R. ;
Subbiah, Jegadesan ;
Small, Cephas E. ;
So, Franky ;
Reynolds, John R. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (26) :10062-10065
[2]   A Series of Fluorene-Based Two-Photon Absorbing Molecules: Synthesis, Linear and Nonlinear Characterization, and Bioimaging [J].
Andrade, Carolina D. ;
Yanez, Ciceron O. ;
Rodriguez, Luis ;
Belfield, Kevin D. .
JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (12) :3975-3982
[3]   Functionalized acenes and heteroacenes for organic electronics [J].
Anthony, John E. .
CHEMICAL REVIEWS, 2006, 106 (12) :5028-5048
[4]   Bipolar Host Materials: A Chemical Approach for Highly Efficient Electrophosphorescent Devices [J].
Chaskar, Atul ;
Chen, Hsiao-Fan ;
Wong, Ken-Tsung .
ADVANCED MATERIALS, 2011, 23 (34) :3876-3895
[5]   Experimental and Theoretical Studies of the Photophysical Properties of 2-and 2,7-Functionalized Pyrene Derivatives [J].
Crawford, Andrew G. ;
Dwyer, Austin D. ;
Liu, Zhiqiang ;
Steffen, Andreas ;
Beeby, Andrew ;
Palsson, Lars-Olof ;
Tozer, David J. ;
Marder, Todd B. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (34) :13349-13362
[6]   Mesomeric and twisted intramolecular-charge-transfer states as a key to polarity-dependent fluorescence of donor-acceptor-substituted aryl pyrenes [J].
Dekhtyar, M. ;
Rettig, W. ;
Weigel, W. .
CHEMICAL PHYSICS, 2008, 344 (03) :237-250
[7]   Strategies to Design Bipolar Small Molecules for OLEDs: Donor-Acceptor Structure and Non-Donor-Acceptor Structure [J].
Duan, Lian ;
Qiao, Juan ;
Sun, Yongduo ;
Qiu, Yong .
ADVANCED MATERIALS, 2011, 23 (09) :1137-1144
[8]   Understanding Energy-Level Alignment in Donor-Acceptor/Metal Interfaces from Core-Level Shifts [J].
El-Sayed, Afaf ;
Borghetti, Patrizia ;
Goiri, Elizabeth ;
Rogero, Celia ;
Floreano, Luca ;
Lovat, Giacoma ;
John Mowbray, Duncan ;
Cabellos, Jose Luis ;
Wakayama, Yutaka ;
Rubio, Angel ;
Enrique Ortega, Jose ;
de Oteyza, Dimas G. .
ACS NANO, 2013, 7 (08) :6914-6920
[9]   Synthesis and Photophysics of Fully π-Conjugated Heterobis-Functionalized Polymeric Molecular Wires via Suzuki Chain-Growth Polymerization [J].
Elmalem, Einat ;
Biedermann, Frank ;
Johnson, Kerr ;
Friend, Richard H. ;
Huck, Wilhelm T. S. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (42) :17769-17777
[10]   Synthesis and photophysical properties of novel butterfly-shaped blue emitters based on pyrene [J].
Feng, Xing ;
Hu, Jian-Yong ;
Tomiyasu, Hirotsugu ;
Seto, Nobuyuki ;
Redshaw, Carl ;
Elsegood, Mark R. J. ;
Yamato, Takehiko .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2013, 11 (48) :8366-8374