Unusual Solid-State Luminescent Push-Pull Indolones: A General One-Pot Three-component Approach

被引:54
作者
D'Souza, Daniel M. [1 ,2 ]
Muschelknautz, Christian [1 ]
Rominger, Frank [2 ]
Mueller, Thomas J. J. [1 ]
机构
[1] Univ Dusseldorf, Inst Organ Chem & Makromol Chem, D-40225 Dusseldorf, Germany
[2] Univ Heidelberg, Inst Organ Chem, D-69120 Heidelberg, Germany
关键词
COUPLING-ISOMERIZATION-STETTER; CATALYZED SEQUENTIAL REACTIONS; DIVERSITY-ORIENTED SYNTHESIS; MULTICOMPONENT REACTIONS; DOMINO-REACTIONS; HIGHLY FLUORESCENT; ORGANIC-SYNTHESIS; EMISSION PROPERTIES; SEQUENCES; CHEMISTRY;
D O I
10.1021/ol101165m
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
In a consecutive three-component cyclocarbopalladation, Sonogashira coupling, Michael addition sequence 4-aminopropenylidene indolones, i.e., terminally fixed push-pull chromophores, are obtained in yields as high as 99%. Most remarkable, however, is the pronounced orange red solid state fluorescence displaying large Stokes shifts of these merocyanines, in particular, since all chromophores are nonfluorescent in solution.
引用
收藏
页码:3364 / 3367
页数:4
相关论文
共 65 条
[21]   A domino sequence consisting of insertion, coupling, isomerization, and Diels-Alder steps yields highly fluorescent spirocycles [J].
D'Souza, DM ;
Rominger, F ;
Müller, TJJ .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (01) :153-158
[22]  
Davydov A. S., 1971, THEORY MOL EXCITONS
[23]   Recent developments in isocyanide based multicomponent reactions in applied chemistry [J].
Dömling, A .
CHEMICAL REVIEWS, 2006, 106 (01) :17-89
[24]  
Dömling A, 2000, ANGEW CHEM INT EDIT, V39, P3168, DOI 10.1002/1521-3773(20000915)39:18<3168::AID-ANIE3168>3.0.CO
[25]  
2-U
[26]   Intermolecular electron transfer in merocyanine aggregates studied by optical and transient EPR methods [J].
Franco, L ;
Pasimeni, L ;
Ponterini, G ;
Ruzzi, M ;
Segre, U .
PHYSICAL CHEMISTRY CHEMICAL PHYSICS, 2001, 3 (09) :1736-1742
[27]   Aggregation-induced emission: phenomenon, mechanism and applications [J].
Hong, Yuning ;
Lam, Jacky W. Y. ;
Tang, Ben Zhong .
CHEMICAL COMMUNICATIONS, 2009, (29) :4332-4353
[28]   Palladium-Catalyzed Sequential Reactions via Allene Intermediates for the Rapid Synthesis of Fused Polycyclic Pyrrole Derivatives [J].
Huang, Xian ;
Zhu, Shugao ;
Shen, Ruwei .
ADVANCED SYNTHESIS & CATALYSIS, 2009, 351 (18) :3118-3122
[29]   Heterocycles as Key Substrates in Multicomponent Reactions: The Fast Lane towards Molecular Complexity [J].
Isambert, Nicolas ;
Lavilla, Rodolfo .
CHEMISTRY-A EUROPEAN JOURNAL, 2008, 14 (28) :8444-8454
[30]   Straightforward novel one-pot enaminone and pyrimidine syntheses by coupling-addition-cyclocondensation sequences [J].
Karpov, AS ;
Müller, TJJ .
SYNTHESIS-STUTTGART, 2003, (18) :2815-2826