N-Annulated Perylene Fused Porphyrins with Enhanced Near-IR Absorption and Emission

被引:92
作者
Jiao, Chongjun [1 ]
Huang, Kuo-Wei [2 ,3 ]
Guan, Zhenping [1 ]
Xu, Qing-Hua [1 ]
Wu, Jishan [1 ]
机构
[1] Natl Univ Singapore, Dept Chem, Singapore 117543, Singapore
[2] 4700 King Abdullah Univ Sci & Technol, KAUST Catalysis Ctr, Thuwal 239556900, Saudi Arabia
[3] 4700 King Abdullah Univ Sci & Technol, Div Chem & Life Sci & Engn, Thuwal 239556900, Saudi Arabia
关键词
2-PHOTON ABSORPTION; PHOTOPHYSICAL PROPERTIES; GRAPHENE NANORIBBONS; FLUORESCENT DYES; 2-STEP SYNTHESIS; CROSS-SECTION; DIPORPHYRINS; ELECTRON; CHROMOPHORES; EXCITATION;
D O I
10.1021/ol1016383
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
N-Annulated perylene fused porphyrins 1 and 2 were synthesized by oxidative dehydrogenation using a Sc(OTf)(3)/DDQ system. These newly synthesized hybrid molecules are highly soluble in organic solvents and exhibit remarkably intense near-IR absorption, as well as detectable photoluminescence quantum yields, all of which are comparable to or even exceed those of either meso-beta doubly linked porphyrin dimer/trimer or bis/tri-N-annulated rylenes.
引用
收藏
页码:4046 / 4049
页数:4
相关论文
共 48 条
[1]   Near-infrared fluorescent materials for sensing of biological targets [J].
Amiot, Carrie L. ;
Xu, Shuping ;
Liang, Song ;
Pan, Lingyun ;
Zhao, Julia Xiaojun .
SENSORS, 2008, 8 (05) :3082-3105
[2]   Exceptional redox and photophysical properties of a triply fused diporphyrin-C60 conjugate:: Novel scaffolds for multicharge storage in molecular scale electronics [J].
Bonifazi, D ;
Scholl, M ;
Song, FY ;
Echegoyen, L ;
Accorsi, G ;
Armaroli, N ;
Diederich, F .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (40) :4966-4970
[3]   Expanding the porphyrin π-system by fusion with anthracene [J].
Davis, Nicola K. S. ;
Pawlicki, Milosz ;
Anderson, Harry L. .
ORGANIC LETTERS, 2008, 10 (18) :3945-3947
[4]   Bis-Anthracene Fused Porphyrins: Synthesis, Crystal Structure, and Near-IR Absorption [J].
Davis, Nicola K. S. ;
Thompson, Amber L. ;
Anderson, Harry L. .
ORGANIC LETTERS, 2010, 12 (09) :2124-2127
[5]   Fused Pyrene-Diporphyrins: Shifting Near-Infrared Absorption to 1.5 μm and Beyond [J].
Diev, Vyacheslav V. ;
Hanson, Kenneth ;
Zimmerman, Jeramy D. ;
Forrest, Stephen R. ;
Thompson, Mark E. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (32) :5523-5526
[6]   NEAR-INFRARED ABSORBING DYES [J].
FABIAN, J ;
NAKAZUMI, H ;
MATSUOKA, M .
CHEMICAL REVIEWS, 1992, 92 (06) :1197-1226
[7]   Quaterrylenebis(dicarboximide)s: near infrared absorbing and emitting dyes [J].
Geerts, Y ;
Quante, H ;
Platz, H ;
Mahrt, R ;
Hopmeier, M ;
Bohm, A ;
Mullen, K .
JOURNAL OF MATERIALS CHEMISTRY, 1998, 8 (11) :2357-2369
[8]   Facile oxidative rearrangement of dispiro-porphodimethenes to nonplanar and sheetlike porphyrins with intense absorptions in the near-IR region [J].
Gill, HS ;
Harmjanz, M ;
Santamaría, J ;
Finger, I ;
Scott, MJ .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (04) :485-490
[9]   From industrial colorants to single photon sources and biolabels:: The fascination and function of rylene dyes [J].
Herrmann, Andreas ;
Muellen, Klaus .
CHEMISTRY LETTERS, 2006, 35 (09) :978-985
[10]  
Hortrup F. O., 1997, CHEM-EUR J, V3, P219