Asymmetric Restriction of Intramolecular Rotation in Chiral Solvents

被引:31
作者
Jin, Young-Jae [1 ]
Kim, Hyojin [1 ,3 ]
Kim, Jong Jin [2 ]
Heo, Nam Ho [2 ]
Shin, Jong Won [4 ]
Teraguchi, Masahiro [5 ,6 ]
Kaneko, Takashi [5 ,6 ]
Aoki, Toshiki [5 ,6 ]
Kwak, Giseop [1 ]
机构
[1] Kyungpook Natl Univ, Major Polymer Sci & Engn, Sch Appl Chem Engn, 1370 Sankyuk Dong, Daegu 702701, South Korea
[2] Kyungpook Natl Univ, Major Appl Chem, Sch Appl Chem Engn, 1370 Sankyuk Dong, Daegu 702701, South Korea
[3] Daegu Technopk Nano Convergence Pract Applicat Ct, 891-5 Daecheon Dong, Daegu 704801, South Korea
[4] POSTECH, Beamline Dept Pohang Accelerator Lab, 80 Jigokro 127 Beongil, Gyeongbuk 37673, South Korea
[5] Niigata Univ, Grad Sch Sci & Technol, Dept Chem & Chem Engn, Nishi Ku, Ikarashi 2-8050, Niigata 9502181, Japan
[6] Niigata Univ, Ctr Transdisciplinary Res, Nishi Ku, Ikarashi 2-8050, Niigata 9502181, Japan
基金
新加坡国家研究基金会;
关键词
AGGREGATION-INDUCED EMISSION; CIRCULARLY-POLARIZED LUMINESCENCE; MOLECULAR-STRUCTURES; SYMMETRY BREAKING; DICHROISM; CRYSTAL; LIGHT; CRYSTALLIZATION; POLYMER; GENERATION;
D O I
10.1021/acs.cgd.6b00128
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Commercially available molecular rotor (MR) compounds were recrystallized using chiral monoterpenes as solvents. The resulting crystals exhibited large circular dichroism signals with opposing signs according to the handedness of the chiral solvent used. X-ray crystallographic analysis showed that the chirality originated from asymmetric restriction of intramolecular rotation in the crystals. The crystals were also highly emissive due to restricted bond rotation, while solutions of the materials were almost nonemissive. The solvent-to-MR chirality transfer approach to. crystallization discussed herein should be a convenient, universal way to obtain highly emissive chiral crystals.
引用
收藏
页码:2804 / 2809
页数:6
相关论文
共 69 条
[1]   2,3,4,5-TETRAPHENYLCYCLOPENTA-2,4-DIEN-1-ONE AND 5,6,7,8-TETRACHLORO-3A,9A-DIHYDRO-2,3,3A,9A-TETRAPHENYLCYCLOPENTA[2,3-B][1,4]BENZODIOXIN-1-ONE-TOLUENE (2/1) - COMPOUNDS OF PHOTOCHEMICAL INTEREST [J].
BARNES, JC ;
HORSPOOL, WM ;
MACKIE, FI .
ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS, 1991, 47 :164-168
[2]  
Barton A.F. M., 1983, CRC HDB SOLUBILITY P
[3]   Reflectance circular dichroism of solid-state chiral coordination compounds [J].
Bilotti, I ;
Biscarini, P ;
Castiglioni, E ;
Ferranti, F ;
Kuroda, R .
CHIRALITY, 2002, 14 (09) :750-756
[4]   CHIRAL DISCRIMINATION OF COMPLEXES WITH D-3 SYMMETRY - SYNTHESIS AND CHARACTERIZATION OF TRIS(O,O'-BIS[(+)(S)-2-METHYLBUTYL] DITHIOPHOSPHATO)CHROMIUM(III) COMPLEXES (LAMBDA-DELTA)(CR[(+)(S)(S)MEBDTP](3)) AND LAMBDA-(-)(589)- AND DELTA-(+)(589)(CR[(+)(S)(S)MEBDTP](3)) AND CRYSTAL PACKING OF RACEMIC TRIS(O,O'-DIETHYL DITHIOPHOSPHATO)CHROMIUM(III), CR[DDTP](3) [J].
BISCARINI, P ;
FRANCA, R ;
KURODA, R .
INORGANIC CHEMISTRY, 1995, 34 (18) :4618-4626
[5]   Detection and memory of nonracemic molecules by a racemic host polymer film [J].
Buono, Anna Maria ;
Immediata, Ivano ;
Rizzo, Paola ;
Guerra, Gaetano .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (36) :10992-+
[6]   Circularly polarized light generated by photoexcitation of luminophores in glassy liquid-crystal films [J].
Chen, SH ;
Katsis, D ;
Schmid, AW ;
Mastrangelo, JC ;
Tsutsui, T ;
Blanton, TN .
NATURE, 1999, 397 (6719) :506-508
[7]   Concentration effects in solid-state CD spectra of chiral atropisomeric compounds [J].
Ding, Lei ;
Lin, Lirong ;
Liu, Chengyong ;
Li, Hongkun ;
Qin, Anjun ;
Liu, Yan ;
Song, Ling ;
Zhang, Hui ;
Tang, Ben Zhong ;
Zhao, Yufen .
NEW JOURNAL OF CHEMISTRY, 2011, 35 (09) :1781-1786
[8]   The J- and H-bands of organic dye aggregates [J].
Eisfeld, A ;
Briggs, JS .
CHEMICAL PHYSICS, 2006, 324 (2-3) :376-384
[9]  
Eliel E. L., 1994, Stereochemistry of Organic Compounds
[10]   METHOD FOR ESTIMATING BOTH SOLUBILITY PARAMETERS AND MOLAR VOLUMES OF LIQUIDS [J].
FEDORS, RF .
POLYMER ENGINEERING AND SCIENCE, 1974, 14 (02) :147-154