Pentacyclic coumarin-based blue emitters - the case of bifunctional nucleophilic behavior of amidines

被引:38
作者
Poronik, Yevgen M. [1 ]
Gryko, Daniel T. [1 ]
机构
[1] Inst Organ Chem PAS, PL-01224 Warsaw, Poland
关键词
FLUORESCENT DYES; DBU; DERIVATIVES; CHEMISTRY; KETONES; ACIDS; UNITS;
D O I
10.1039/c4cc01106f
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
An unexpected discovery of the novel cyclocondensation reaction of 1,8-diazabicyclo[5.4.0] undec-8-ene (DBU) and 1,5-diazabicyclo-[4.3.0] non-5-ene (DBN) with alkyl coumarin-3-carboxylates is described. First, an unknown skeleton is generated through the concomitant formation of new nitrogen-carbon and carbon-carbon bonds followed by the oxidation of the intermediate product by the second equivalent of the starting coumarin. Pentacyclic DBN-derivatives exhibit strong fluorescence both in solutions (Phi(fl) similar to 0.6-0.8) and in the solid state, while non-planar DBU-derivatives exhibit strong fluorescence in the solid state only.
引用
收藏
页码:5688 / 5690
页数:3
相关论文
共 44 条
[1]   Light harvesting and energy transfer in laser-dye-labeled poly(aryl ether) dendrimers [J].
Adronov, A ;
Gilat, SL ;
Fréchet, JMJ ;
Ohta, K ;
Neuwahl, FVR ;
Fleming, GR .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (06) :1175-1185
[2]   SYNTHESIS OF MEDIUM-RING BICYCLIC DIAMINES BY THE ALKYLATION AND CLEAVAGE OF CYCLIC AMIDINES [J].
ALDER, RW ;
SESSIONS, RB .
TETRAHEDRON LETTERS, 1982, 23 (10) :1121-1124
[3]   π-Conjugated Cyanostilbene Derivatives: A Unique Self-Assembly Motif for Molecular Nanostructures with Enhanced Emission and Transport [J].
An, Byeong-Kwan ;
Gierschner, Johannes ;
Park, Soo Young .
ACCOUNTS OF CHEMICAL RESEARCH, 2012, 45 (04) :544-554
[4]   Nucleophilicities and carbon basicities of DBU and DBN [J].
Baidya, M. ;
Mayr, Herbert .
CHEMICAL COMMUNICATIONS, 2008, (15) :1792-1794
[5]   Recent advances in the Baylis-Hillman reaction and applications [J].
Basavaiah, D ;
Rao, AJ ;
Satyanarayana, T .
CHEMICAL REVIEWS, 2003, 103 (03) :811-891
[6]   1,8-DIAZABICYCLO[5.4.0]UNDEC-7-ENE AS A DIFUNCTIONAL NUCLEOPHILE [J].
CHAMBERS, RD ;
ROCHE, AJ ;
BATSANOV, AS ;
HOWARD, JAK .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1994, (18) :2055-2056
[7]   Molecular design and synthesis of N-arylsulfonated coumarin fluorescent dyes and their application to textiles [J].
Christie, Robert M. ;
Morgan, Keith M. ;
Islam, M. Saiful .
DYES AND PIGMENTS, 2008, 76 (03) :741-747
[8]   Synthesis of Coumarins via Pd-Catalyzed Oxidative Cyclocarbonylation of 2-Vinylphenols [J].
Ferguson, Jamie ;
Zeng, Fanlong ;
Alper, Howard .
ORGANIC LETTERS, 2012, 14 (21) :5602-5605
[9]   From bifunctional nucleophilic behavior of DBU to a new heterocyclic fluorescent platform [J].
Gryko, Daniel T. ;
Piechowska, Joanna ;
Tasior, Mariusz ;
Waluk, Jacek ;
Orzanowska, Grazyna .
ORGANIC LETTERS, 2006, 8 (21) :4747-4750
[10]   Fluorescent Dyes with 2-Amino-4,7-diazaindole Skeleton: Synthesis and Spectroscopy [J].
Gryko, Daniel T. ;
Piechowska, Joanna ;
Vetokhina, Volha ;
Wojcik, Dominik .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 2009, 82 (12) :1514-1519