Oligoindenopyrenes: A new class of polycyclic aromatics

被引:79
作者
Wegner, Hermann A.
Reisch, Helge
Rauch, Karsten
Demeter, Attila
Zachariasse, Klaas A.
de Meijere, Armin
Scott, Lawrence T. [1 ]
机构
[1] Boston Coll, Merkert Chem Ctr, Chestnut Hill, MA 02467 USA
[2] Univ Gottingen, Inst Organ & Biomol Chem, D-37077 Gottingen, Germany
[3] Max Planck Inst Biophys Chem, Abt Spektroskopie & Photochem Kinet, D-37077 Gottingen, Germany
[4] Hungarian Acad Sci, Inst Struct Chem, Chem Res Ctr, H-1525 Budapest, Hungary
关键词
D O I
10.1021/jo0613939
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A new class of polycyclic aromatic hydrocarbons-oligoindenopyrenes-has been synthesized featuring a Pd-catalyzed Suzuki-Heck coupling cascade. The oligoindenopyrenes are robust, highly colored substructures of C-70 and have properties that might prove useful in new organic materials or devices. After excitation, the tetraindenopyrene derivative 3d undergoes efficient deactivation ( 99%) by internal conversion to the ground state. The small fluorescence quantum yield ( 0.004) is in accordance with the short ( 0.6 ns) fluorescence decay time.
引用
收藏
页码:9080 / 9087
页数:8
相关论文
共 26 条
[1]  
APRAHAMIAN I, IN PRESS CHEM ASIAN
[2]   BACTERIAL MUTAGENICITY OF NEW CYCLOPENTA-FUSED CATA-ANNELATED POLYCYCLIC AROMATIC-HYDROCARBONS, AND IDENTIFICATION OF THE MAJOR METABOLITES OF BENZ[J]ACEPHENANTHRYLENE FORMED BY AROCLOR-TREATED RAT-LIVER MICROSOMES [J].
BALL, LM ;
WARREN, SH ;
SANGAIAH, R ;
NESNOW, S ;
GOLD, A .
MUTATION RESEARCH, 1989, 224 (01) :115-125
[3]  
Berlman I.B., 1971, Handbook of Fluorescence Spectra of Aromatic Molecules
[4]  
BIRKS JB, 1970, PHOTPHYSICS AROMATIC
[5]   POLYCYCLIC FLUORANTHENE HYDROCARBONS .2. A NEW GENERAL-SYNTHESIS [J].
CHO, BP ;
HARVEY, RG .
JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (26) :5668-5678
[6]  
DEMAS JN, 1971, J PHYS CHEM-US, V75, P991, DOI 10.1021/j100678a001
[7]   Dynamics of ultrafast intramolecular charge transfer with 4-(dimethylamino)benzonitrile in acetonitrile [J].
Druzhinin, SI ;
Ernsting, NP ;
Kovalenko, SA ;
Lustres, LW ;
Senyushkina, TA ;
Zachariasse, KA .
JOURNAL OF PHYSICAL CHEMISTRY A, 2006, 110 (09) :2955-2969
[8]   Thermally activated internal conversion with 4-(dimethylamino)benzonitrile, 4-(methylamino)benzonitrile, and 4-aminobenzonitrile in alkane solvents. No correlation with intramolecular charge transfer [J].
Druzhinin, SI ;
Demeter, A ;
Galievsky, VA ;
Yoshihara, T ;
Zachariasse, KA .
JOURNAL OF PHYSICAL CHEMISTRY A, 2003, 107 (40) :8075-8085
[9]   ENERGY GAP LAW FOR RADIATIONLESS TRANSITIONS IN LARGE MOLECULES [J].
ENGLMAN, R ;
JORTNER, J .
MOLECULAR PHYSICS, 1970, 18 (02) :145-+
[10]   Synthesis of C3 Benzo[1,2-e:3,4-e':5,6-e"]tribenzo[l]acephenanthrylenes (Crushed fullerene derivatives) by intramolecular palladium-catalyzed arylation [J].
Gómez-Lor, B ;
González-Cantalapiedra, E ;
Ruiz, M ;
de Frutos, S ;
Cárdenas, DJ ;
Santos, A ;
Echavarren, AM .
CHEMISTRY-A EUROPEAN JOURNAL, 2004, 10 (10) :2601-2608