Regiocontrolled Synthesis of Ethene-Bridged para-Phenylene Oligomers Based on PtII- and RuII-Catalyzed Aromatization

被引:49
作者
Chen, Tse-An [1 ]
Lee, Te-Ju [2 ]
Lin, Ming-Yuan [1 ]
Sohel, Shariar M. A. [1 ]
Dian, Eric Wei-Guang [2 ]
Lush, Shie-Fu [3 ]
Liu, Rai-Shung [1 ]
机构
[1] Natl Tsing Hua Univ, Dept Chem, Hsinchu 30013, Taiwan
[2] Natl Chiao Tung Univ, Dept Appl Chem, Hsinchu 30010, Taiwan
[3] Yuanpei Univ, Dept Med Technol, Hsinchu 30015, Taiwan
关键词
catalysis; platinum; polyaromatic oligomers; regiocontrol; ruthenium; DISCOTIC LIQUID-CRYSTALS; ORGANIC ELECTRONICS; CONJUGATED POLYMERS; GRAPHITE RIBBONS; CYCLOISOMERIZATION; DERIVATIVES; HEPTACENE; ACENES; PHENANTHRENES; HYDROCARBONS;
D O I
10.1002/chem.200902231
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
We report the regiocontrolled syntheses of ethene-bridged para-phenylene oligomers in three distinct classes by using Pt-II- and Ru-II-catalyzed aromatization. This synthetic approach has been developed based on twofold aromatization of the 1-aryl-2-alkynyl-benzene functionality, which proceeds by distinct regioselectivity for platinum and ruthenium catalysts. Variable-temperature NMR spectra provide evidence that large arrays of these oligomers are prone to twist from planarity. The UV/Vis and photoluminescence (PL) spectra as well as the band gaps of these regularly growing arrays show a pattern of extensive pi conjugation with increasing array sizes, except for in one instance.
引用
收藏
页码:1826 / 1833
页数:8
相关论文
共 56 条
[1]  
[Anonymous], ANGEW CHEM
[2]   Functionalized acenes and heteroacenes for organic electronics [J].
Anthony, John E. .
CHEMICAL REVIEWS, 2006, 106 (12) :5028-5048
[3]  
Baird T., 1988, CHEM COMMUN, P1471
[4]   Tetrathiafulvalenes, oligoacenenes, and their buckminsterfullerene derivatives: The brick and mortar of organic electronics [J].
Bendikov, M ;
Wudl, F ;
Perepichka, DF .
CHEMICAL REVIEWS, 2004, 104 (11) :4891-4945
[5]   Polycyclic aromatic hydrocarbons by ring-closing metathesis [J].
Bonifacio, MC ;
Robertson, CR ;
Jung, JY ;
King, BT .
JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (21) :8522-8526
[6]   Relaxation dynamics of ruthenium complexes in solution, PMMA and TiO2 films:: The roles of self-quenching and interfacial electron transfer [J].
Chang, Chih-Wei ;
Chou, Chung Kuang ;
Chang, I-Jy ;
Lee, Yuan-Pern ;
Diau, Eric Wei-Guang .
JOURNAL OF PHYSICAL CHEMISTRY C, 2007, 111 (35) :13288-13296
[7]  
Chun D., 2008, ANGEW CHEM, V120, P8508
[8]   The Most Stable and Fully Characterized Functionalized Heptacene [J].
Chun, Doris ;
Cheng, Yang ;
Wudl, Fred .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (44) :8380-8385
[9]   Ruthenium-catalyzed cycloisomerization of cis-3-en-1-ynes to cyclopentadiene and related derivatives through a 1,5-sigmatropic hydrogen shift of ruthenium-vinylidene intermediates [J].
Datta, S ;
Odedra, A ;
Liu, RS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (33) :11606-11607
[10]   Elaboration of diaryl ketones into naphthalenes fused on two or four sides: A naphthoannulation procedure [J].
Donovan, PM ;
Scott, LT .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (10) :3108-3112