Helical Oligonaphthodioxepins Showing Intense Circularly Polarized Luminescence (CPL) in Solution and in the Solid State

被引：56

作者：

Takaishi, Kazuto ^{[1
]}

Yamamoto, Takahiro ^{[1
]}

Hinoide, Sakiko ^{[1
]}

Ema, Tadashi ^{[1
]}

机构：

[1] Okayama Univ, Grad Sch Nat Sci & Technol, Div Appl Chem, Okayama 7008530, Japan

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2017年 / 23卷 / 39期

关键词：

axial chirality; chiroptical property; circularly polarized luminescence; helical structures; CHIROPTICAL PROPERTIES; 2-STEP SYNTHESIS; LIQUID-CRYSTAL; MOLECULES; CHIRALITY; BODIPY; LUMINOPHORES; FLUORESCENCE; ASSEMBLIES; ABSORPTION;

D O I：

10.1002/chem.201702143

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A series of oligonaphthodioxepins was synthesized, revealing a helically arranged octamer, (R,R,R,R,R,R,R)-3, which showed intense circularly polarized luminescence (CPL) both in solution and in the solid state. The fluorescence quantum yields (Phi(FL)) in solution and in the solid state were 0.90 and 0.22, respectively, and the glum values in solution and in the solid state were vertical bar 2.2 x 10 (-3) 3 and + 7.0 x 10 (-3) , respectively. This is one of the highest solid-state CPL glum values yet reported. The high FFL and glum values were due to the rigidity, as well as to the fact that (R, R, R, R, R, R, R)-3 was a non-planar molecule. Moreover, (R, R, R, R, R, R, R)-3 was highly stable both chemically and stereochemically.

引用

页码：9249 / 9252

页数：4

共 45 条

[1] Circularly Polarized Luminescence from Helically Chiral N,N,O,O-Boron-Chelated Dipyrromethenes
Alnoman, Rua B.
Rihn, Sandra
O'Connor, Daniel C.
Black, Fiona A.
Costello, Bernard
Waddell, Paul G.
Clegg, William
Peacock, Robert D.
Herrebout, Wouter
Knight, Julian G.
Hall, Michael J.
[J]. CHEMISTRY-A EUROPEAN JOURNAL, 2016, 22 (01) : 93 - 96
[2] Solid-state circularly polarised luminescence of atropisomeric fluorophores embedded in achiral myo-inositol-containing polyurethanes
Amako, Tomoyuki
Nakabayashi, Kazuki
Sudo, Atsushi
Fujiki, Michiya
Imai, Yoshitane
[J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2015, 13 (10) : 2913 - 2917
[3] [Anonymous], 2013, ANGEW CHEM
[4] Functionalized cationic [4] helicenes with unique tuning of absorption, fluorescence and chiroptical properties up to the far-red range
Delgado, I. Hernandez
Pascal, S.
Wallabregue, A.
Duwald, R.
Besnard, C.
Guenee, L.
Nancoz, C.
Vauthey, E.
Tovar, R. C.
Lunkley, J. L.
Muller, G.
Lacour, J.
[J]. CHEMICAL SCIENCE, 2016, 7 (07) : 4685 - 4693
[5] Fan J., 2015, ANGEW CHEM, V127, P2188, DOI DOI 10.1002/ANGE.201410788
[6] Light-Directing Omnidirectional Circularly Polarized Reflection from Liquid-Crystal Droplets
Fan, Jing
Li, Yannian
Bisoyi, Hari Krishna
Zola, Rafael S.
Yang, Deng-ke
Bunning, Timothy J.
Weitz, David A.
Li, Quan
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (07) : 2160 - 2164
[7] Design and Synthesis of New Circularly Polarized Thermally Activated Delayed Fluorescence Emitters
Feuillastre, Sophie
Pauton, Mathilde
Gao, Longhui
Desmarchelier, Alaric
Riives, Adrian J.
Prim, Damien
Tondelier, Denis
Geffroy, Bernard
Muller, Gilles
Clavier, Gilles
Pieters, Gregory
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2016, 138 (12) : 3990 - 3993
[8] Frisch M. J., 2009, DFT calculations were performed using Gaussian 09, Revision D. 01
[9] Synthesis and Chiroptical Properties of a Ring-Fused BODIPY with a Skewed Chiral π Skeleton
Gobo, Yuki
Yamamura, Masaki
Nakamura, Takashi
Nabeshima, Tatsuya
[J]. ORGANIC LETTERS, 2016, 18 (11) : 2719 - 2721
[10] GON M, 2017, MACROMOLECULES, V50, P1790

← 1 2 3 4 5 →