Core-functionalized dendritic oligothiophenes-novel donor-acceptor systems

被引:27
作者
Fischer, Markus K. R. [1 ]
Ma, Chang-Qi [1 ]
Janssen, Rene A. J. [2 ]
Debaerdemaeker, Tony [3 ]
Baeuerle, Peter [1 ]
机构
[1] Univ Ulm, Inst Organ Chem & Adv Mat 2, D-89081 Ulm, Germany
[2] Eindhoven Univ Technol, NL-5600 MB Eindhoven, Netherlands
[3] Univ Ulm, Inst Inorgan Chem 1, D-89081 Ulm, Germany
关键词
HETEROJUNCTION SOLAR-CELLS; STAR-SHAPED OLIGOTHIOPHENES; POLY(BENZYL ETHER) DENDRONS; INTERNAL CHARGE-TRANSFER; ELECTROCHEMICAL PROPERTIES; PHOTOVOLTAIC DEVICES; ORGANIC ELECTRONICS; CONJUGATED POLYMERS; OPTICAL-PROPERTIES; DENDRIMERS;
D O I
10.1039/b904243a
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
Novel core-functionalized dendritic oligothiophenes (DOT) bearing pyridine or methylpyridinium acceptors have been synthesized up to the third generation. A bathochromic shift in the absorption of the functionalized dendritic oligothiophenes and the appearance of new absorption bands were noticed issuing from an intramolecular charge transfer process. These novel donor-acceptor systems are, due to their broad absorption, promising materials for optoelectronic applications such as organic solar cells. By electrochemical measurements HOMO/LUMO energy levels have been determined and two compounds could be identified with almost ideal energy levels for application in bulk heterojunction solar cells (BHJSC) with fullerene PC61BM as acceptor.
引用
收藏
页码:4784 / 4795
页数:12
相关论文
共 53 条
[1]   Facile, regioselective synthesis of highly solvatochromic thiophene-spaced N-alkylpyridinium dicyanomethanides for second-harmonic generation [J].
Abbotto, A ;
Bradamante, S ;
Facchetti, A ;
Pagani, GA .
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (17) :5755-5765
[2]  
Adams N., 1969, ELECTROCHEMISTRY SOL
[3]   Synthesis and steady-state photophysical properties of dye-labeled dendrimers having novel oligothiophene cores:: A comparative study [J].
Adronov, A ;
Malenfant, PRL ;
Fréchet, JMJ .
CHEMISTRY OF MATERIALS, 2000, 12 (05) :1463-1472
[4]   PREPARATION OF EXTENDED DI(4-PYRIDYL)THIOPHENE OLIGOMERS [J].
ALBERS, WM ;
CANTERS, GW ;
REEDIJK, J .
TETRAHEDRON, 1995, 51 (13) :3895-3904
[5]   Redox states of well-defined π-conjugated oligothiophenes functionalized with poly(benzyl ether) dendrons [J].
Apperloo, JJ ;
Janssen, RAJ ;
Malenfant, PRL ;
Groenendaal, L ;
Fréchet, JMJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (29) :7042-7051
[6]   The structural role of the triflate anion in the non-covalent silver polymer [Ag(LOH)2(CF3SO3)(CH3CN)] {LOH = α-(4-pyridyl)benzhydrol} [J].
Bacchi, A ;
Bosetti, E ;
Carcelli, M ;
Pelagatti, P ;
Rogolino, D .
EUROPEAN JOURNAL OF INORGANIC CHEMISTRY, 2004, (10) :1985-1991
[7]   Polyphenylene nanostructures [J].
Berresheim, AJ ;
Müller, M ;
Müllen, K .
CHEMICAL REVIEWS, 1999, 99 (07) :1747-1785
[8]   Swivel-cruciform oligothiophene dimers [J].
Bilge, Askin ;
Zen, Achmad ;
Forster, Michael ;
Li, Hongbo ;
Galbrecht, Frank ;
Nehls, Benjamin S. ;
Farrell, Tony ;
Neher, Dieter ;
Scherf, Ullrich .
JOURNAL OF MATERIALS CHEMISTRY, 2006, 16 (31) :3177-3182
[9]   On the use of cyanine dyes as low-bandgap materials in bulk heterojunction photovoltaic devices [J].
Castro, Fernando A. ;
Faes, Antonin ;
Geiger, Thomas ;
Graeff, Carlos F. O. ;
Nagel, Matthias ;
Nueesch, Frank ;
Hany, Roland .
SYNTHETIC METALS, 2006, 156 (14-15) :973-978
[10]   SOLVATOCHROMISM OF A TYPICAL MEROCYANINE - STILBAZOLIUM BETAINE AND ITS 2,6-DI-TERT-BUTYL DERIVATIVE [J].
CATALAN, J ;
MENA, E ;
MEUTERMANS, W ;
ELGUERO, J .
JOURNAL OF PHYSICAL CHEMISTRY, 1992, 96 (09) :3615-3621