Construction of chiral through-space luminophores via symmetry breaking triggered by sequenced chlorination

Xie，Yufeng1,2; Liu，Huaying1; Li，Zhongliang3; Zhang，Xin4; Song，Lijuan1; Zhou，Kang5; Yuan，Feng1; You，Hengzhi1,2; Zhao，Engui1; He，Zikai1,2

2023

10.1007/s11426-023-1560-0

Science China Chemistry   影响因子和分区

1674-7291

1869-1870

The construction of molecular chirality is crucial for exploring novel luminophores with chiroptical properties. Classic asymmetric synthesis of chiral center or axial is not powerful enough on through-space architecture. Accessible methodologies for breaking molecular symmetry could be promising but remain less investigated. Herein, we report a novel methodology for constructing chiral through-space luminophores via simple chlorination on bridged carbazole motifs. The chlorination breaks the molecular symmetry and thus results in molecular chirality by eliminating the mirror plane or rotating axis. Interestingly, continuous multiple chlorinations can rebuild and break the symmetry of the skeleton in succession. Several chiral and achiral isomeric analogues are synthesized and characterized with impressive chiroptical properties. Results of chiral high performance liquid chromatography (HPLC), single-crystal X-ray diffraction, kinetic racemization, and chiroptical property investigation demonstrate the effectiveness of our rational design strategy. It provides a feasible methodology for exploring novel chiral luminescent materials based on versatile though-space skeletons.

chiral through-space luminophore circularly-polarized luminescence kinetic racemization symmetry breaking

SCI ; EI

英语

其他

National Natural Science Foundation of China[21975061] ; Shenzhen Fundamental Research Program["JCYJ20190806142403535","GXWD2020123015542700 320200728150952003"]

Chemistry

Chemistry, Multidisciplinary

WOS:000991553700003

SCIENCE PRESS

20232114117525

Chirality ; Chlorination ; High performance liquid chromatography ; Luminescence ; Single crystals

Biomechanics, Bionics and Biomimetics:461.3 ; Light/Optics:741.1 ; Chemical Reactions:802.2 ; Atomic and Molecular Physics:931.3 ; Crystalline Solids:933.1

2-s2.0-85159588597

Scopus

1.School of Science,Harbin Institute of Technology,Shenzhen,518055,China
2.School of Chemical Engineering and Technology,Harbin Institute of Technology Harbin,Harbin,150001,China
3.Academy for Advanced Interdisciplinary Studies and Department of Chemistry,Southern University of Science and Technology,Shenzhen,518055,China
4.Shenzhen Bay Laboratory,Shenzhen,518055,China
5.Hoffmann Institute of Advanced Materials,Shenzhen Polytechnic,Shenzhen,518055,China

Xie，Yufeng,Liu，Huaying,Li，Zhongliang,et al. Construction of chiral through-space luminophores via symmetry breaking triggered by sequenced chlorination[J]. Science China Chemistry,2023,66(7):2083-2090.

Xie，Yufeng.,Liu，Huaying.,Li，Zhongliang.,Zhang，Xin.,Song，Lijuan.,...&He，Zikai.(2023).Construction of chiral through-space luminophores via symmetry breaking triggered by sequenced chlorination.Science China Chemistry,66(7),2083-2090.

Xie，Yufeng,et al."Construction of chiral through-space luminophores via symmetry breaking triggered by sequenced chlorination".Science China Chemistry 66.7(2023):2083-2090.