Solid-State Chiral Supramolecular Organic Fluorophore Having a π-Conjugated Phenylene Ethynylene Unit

被引:19
作者
Kinuta, Takafumi [1 ]
Kamon, Kensaku [1 ]
Harada, Takunori [2 ]
Nakano, Yoko [3 ]
Tajima, Nobuo [4 ]
Sato, Tomohiro [2 ]
Fujiki, Michiya [3 ]
Kuroda, Reiko [2 ,5 ]
Matsubara, Yoshio [1 ]
Imai, Yoshitane [1 ]
机构
[1] Kinki Univ, Fac Sci & Engn, Dept Appl Chem, Higashiosaka, Osaka 5778502, Japan
[2] JST ERATO SORST Kuroda Chiromorphol Team, Meguro Ku, Tokyo 1530041, Japan
[3] Nara Inst Sci & Technol, Grad Sch Mat Sci, Nara 6300192, Japan
[4] Natl Inst Mat Sci, Principles Simulat Grp 1, Computat Mat Sci Ctr, Tsukuba, Ibaraki 3050047, Japan
[5] Univ Tokyo, Dept Life Sci, Grad Sch Arts & Sci, Meguro Ku, Tokyo 1538902, Japan
关键词
Chirality; Luminescence; Conjugation; Fluorophores; Supramolecular chemistry; QUINOL-TYPE FLUOROPHORES; PHOTOPHYSICAL PROPERTIES; MOLECULAR INFORMATION; HOST SYSTEM; FLUORESCENCE; ACID; DERIVATIVES; 2,5-DIBORYL-1,4-PHENYLENE; TRANSCRIPTION; TRANSLATION;
D O I
10.1002/ejoc.200900782
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A solid-state, chiral, helical, columnar, organic fluorophore having a pi-conjugated phenylene ethynylene unit was prepared by using 4-[2-(4-methylphenyl)ethynyl]benzoic acid and 1-phenylethylamine. Such a chiral pi-conjugated organic fluorophore can be obtained from achiral and racemic component molecules, and it exhibits circularly polarized luminescence (CPL) in the solid state. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)
引用
收藏
页码:5760 / 5764
页数:5
相关论文
共 31 条
[1]  
[Anonymous], 1999, PLATON MOL GEOMETRY
[2]   DENSITY-FUNCTIONAL THERMOCHEMISTRY .3. THE ROLE OF EXACT EXCHANGE [J].
BECKE, AD .
JOURNAL OF CHEMICAL PHYSICS, 1993, 98 (07) :5648-5652
[3]   Preparation of a spontaneous resolution chiral fluorescent system using 2-anthracenecarboxylic acid [J].
Imai, Yoshitane ;
Kamon, Kensaku ;
Murata, Katuzo ;
Harada, Takunori ;
Nakano, Yoko ;
Sato, Tornohiro ;
Fujiki, Michiya ;
Kuroda, Reiko ;
Matsubara, Yoshio .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2008, 6 (19) :3471-3475
[4]   Multiple molecular response columnar host system composed of rac-2-amino-1,2-diphenylethanol and 1-fluorenecarboxylic acid [J].
Imai, Yoshitane ;
Nagasaki, Keiko ;
Murata, Katuzo ;
Kawaguchi, Kakuhiro ;
Harada, Takunori ;
Nakano, Yoko ;
Sato, Tomohiro ;
Fujiki, Michiya ;
Kuroda, Reiko ;
Matsubara, Yoshio .
CRYSTENGCOMM, 2008, 10 (08) :951-953
[5]   A solid-state fluorescent host system with a 21-helical column consisting of chiral (1R,2S)-2-amino-1,2-diphenylethanol and fluorescent 1-pyrenecarboxylic acid [J].
Imai, Yoshitane ;
Murata, Katuzo ;
Kawaguchi, Kakuhiro ;
Sato, Tomohiro ;
Tajima, Nobuo ;
Kuroda, Reiko ;
Matsubara, Yoshio .
CHEMISTRY-AN ASIAN JOURNAL, 2008, 3 (03) :625-629
[6]   Solid-state optical properties of a chiral supramolecular fluorophore consisting of chiral (1R,2R)-1,2-diphenylethylenediamine and fluorescent carboxylic acid derivatives [J].
Imai, Yoshitane ;
Kawaguchi, Kakuhiro ;
Harada, Takunori ;
Sato, Tomohiro ;
Ishikawa, Masaaki ;
Fujiki, Michiya ;
Kuroda, Reiko ;
Matsubara, Yoshio .
TETRAHEDRON LETTERS, 2007, 48 (16) :2927-2930
[7]   SOLID-STATE CIRCULAR-DICHROISM SPECTRA OF TRIS(DIAMINE)COBALT(III) COMPLEXES - DECOMPOSITION INTO E-COMPONENTS AND A2-COMPONENTS [J].
KURODA, R ;
SAITO, Y .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1976, 49 (02) :433-436
[8]   THE INFLUENCE OF PACKING EFFECTS ON THE SOLID-STATE FLUORESCENCE OF DIKETOPYRROLOPYRROLES [J].
LANGHALS, H ;
POTRAWA, T ;
NOTH, H ;
LINTI, G .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1989, 28 (04) :478-480
[9]   Persistent fluorescence of perylene dyes by steric inhibition of aggregation [J].
Langhals, H ;
Ismael, R ;
Yürük, O .
TETRAHEDRON, 2000, 56 (30) :5435-5441
[10]   Highly Fluorescent Rigid Supramolecular Polymeric Nanowires Constructed Through Multiple Hydrogen Bonds [J].
Luo, Jia ;
Lei, Ting ;
Wang, Lei ;
Ma, Yuguo ;
Cao, Yong ;
Wang, Jian ;
Pei, Jian .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (06) :2076-+