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

来源：

ORGANIC LETTERS | 2010年 / 12卷 / 18期

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

页码：4046 / 4049

页数：4

共 48 条

[21] Porphyrins with exocyclic rings. 16. Synthesis and spectroscopic characterization of fluoranthoporphyrins, a new class of highly conjugated porphyrin chromophores [J].

Lash, TD ;

Werner, TM ;

Thompson, ML ;

Manley, JM .

JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (09) :3152-3159

[22] Rainbow Perylene Monoimides: Easy Control of Optical Properties [J].

Li, Chen ;

Schoeneboom, Jan ;

Liu, Zhihong ;

Pschirer, Neil G. ;

Erk, Peter ;

Herrmann, Andreas ;

Muellen, Klaus .

CHEMISTRY-A EUROPEAN JOURNAL, 2009, 15 (04) :878-884

[23] Tri-N-annulated Hexarylene: An Approach to Well-Defined Graphene Nanoribbons with Large Dipoles [J].

Li, Yan ;

Gao, Jing ;

Di Motta, Simone ;

Negri, Fabrizia ;

Wang, Zhaohui .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (12) :4208-4213

[24] Bis-N-Annulated Quaterrylene: An Approach to Processable Graphene Nanoribbons [J].

Li, Yan ;

Wang, Zhaohui .

ORGANIC LETTERS, 2009, 11 (06) :1385-1387

[25] MONONITRATION OF PERYLENE - PREPARATION AND STRUCTURE PROOF OF 1 AND 3 ISOMERS [J].

LOOKER, JJ .

JOURNAL OF ORGANIC CHEMISTRY, 1972, 37 (21) :3379-&

[26] A tightly coupled linear array of perylene, bis(porphyrin), and phthalocyanine units that functions as a photoinduced energy-transfer cascade [J].

Miller, MA ;

Lammi, RK ;

Prathapan, S ;

Holten, D ;

Lindsey, JS .

JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (20) :6634-6649

[27] Directly meso-meso linked porphyrin rings:: Synthesis, characterization, and efficient excitation energy hopping [J].

Nakamura, Y ;

Hwang, IW ;

Aratani, N ;

Ahn, TK ;

Ko, DM ;

Takagi, A ;

Kawai, T ;

Matsumoto, T ;

Kim, D ;

Osuka, A .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (01) :236-246

[28] Synthesis and modification of terrylenediimides as high-performance fluorescent dyes [J].

Nolde, F ;

Qu, JQ ;

Kohl, C ;

Pschirer, NG ;

Reuther, E ;

Müllen, K .

CHEMISTRY-A EUROPEAN JOURNAL, 2005, 11 (13) :3959-3967

[29] PICOSECOND OPTICAL SWITCHING BASED ON BIPHOTONIC EXCITATION OF AN ELECTRON DONOR-ACCEPTOR-DONOR MOLECULE [J].

ONEIL, MP ;

NIEMCZYK, MP ;

SVEC, WA ;

GOSZTOLA, D ;

GAINES, GL ;

WASIELEWSKI, MR .

SCIENCE, 1992, 257 (5066) :63-65

[30] Two-Photon Absorption and the Design of Two-Photon Dyes [J].

Pawlicki, Milosz ;

Collins, Hazel A. ;

Denning, Robert G. ;

Anderson, Harry L. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (18) :3244-3266

← 1 2 3 4 5 →