Citation: Guiyang Xia, Lingyan Wang, Huan Xia, Yuzhuo Wu, Yanan Wang, Haiyu Hu, Sheng Lin. Circularly polarized luminescence of talarolactones (+)/(−)-A and (+)/(−)-C: The application of CPL-calculation in stereochemical assignment[J]. Chinese Chemical Letters, ;2022, 33(9): 4253-4256. doi: 10.1016/j.cclet.2022.03.032 shu

Circularly polarized luminescence of talarolactones (+)/(−)-A and (+)/(−)-C: The application of CPL-calculation in stereochemical assignment

Guiyang Xia ^a ,
Lingyan Wang ^a ,
Huan Xia ^a ,
Yuzhuo Wu ^a ,
Yanan Wang ^b ,
Haiyu Hu ^{b, *,} ,
Sheng Lin ^{a, c, **,}

a.
Key Laboratory of Chinese Internal Medicine of Ministry of Education and Beijing, Dongzhimen Hospital, Beijing University of Chinese Medicine, Beijing 100700, China
b.
State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100050, China
c.
Key Laboratory for Qinghai-Tibet Plateau Phytochemistry of Qinghai Province, College of Pharmaceutical, Qinghai Nationalities University, Xining 810007, China

haiyu.hu@imm.ac.cn

lsznn@bucm.edu.cn

Received Date: 5 February 2022
Revised Date: 8 March 2022
Accepted Date: 8 March 2022
Available Online: 11 March 2022

Figures(6)

Two pairs of fluorescent natural products, talarolactones (+)/(−)-A and (+)/(−)-C [(+)/(−)-1 and (+)/(−)-2], were discovered and characterized as a new family of circularly polarized luminescence-active small organic molecules (CPL-SOMs) with high fluorescence efficiency and fascinating CPL properties. The CPL (|g_lum|) levels of enantiomerically pure (+)/(−)-1 and (+)/(−)-2 in solution falls into the usual range (10⁻⁵−10⁻³) considering their pure organic nature, but the sign of CPL were found to be closely related to the absolute configuration of C-8. The high agreement of the measured CPL spectra of (+)/(−)-1 and (+)/(−)-2 with the time-dependent density functional theory (TDDFT) calculated ones demonstrated the usefulness of CPL-calculation as a unique method for stereochemical assignment. This study may open up a new perspective for the stereochemical studies and the future development of CPL materials.
- Circularly polarized luminescence,
- Natural products,
- Stereochemical assignment,
- Talarolactones (+)/(−)-A,
- Talarolactones (+)/(−)-C
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