Pillar[5]arene-based Neutral Radicals with Doublet Red Emissions and Stable Chiroptical Properties

Jin Fa Chen; Guoqing Tian; Kanglei Liu; Niu Zhang; Nan Wang; Xiaodong Yin; Pangkuan Chen

doi:10.1021/acs.orglett.2c00313

Pillar[5]arene-based Neutral Radicals with Doublet Red Emissions and Stable Chiroptical Properties

Jin Fa Chen, Guoqing Tian, Kanglei Liu, Niu Zhang, Nan Wang, Xiaodong Yin, Pangkuan Chen^*

^*Corresponding author for this work

School of Chemistry and Chemical Engineering

Beijing Institute of Technology

Research output: Contribution to journal › Article › peer-review

43 Citations (Scopus)

Abstract

Stable organic radicals with unique luminescence show great importance in photoelectromagnetic materials. We herein report two unusual radical-based systems (P5N-TTM and P5B-TTM) using the concerted effects of planar chiral pillar[5]arenes and tris(2,4,6-trichlorophenyl)methyl (TTM) radicals. The steric effect and electronic doublet-spin character of these radicals allowed the optical resolution and the first red emissions (∼650 nm) for pillar[5]arene derivatives. Notably, cross-coupling with macrocyclic pillar[5]arene, in turn, considerably enhanced the configurational stability of TTM radicals.

Original language	English
Pages (from-to)	1935-1940
Number of pages	6
Journal	Organic Letters
Volume	24
Issue number	10
DOIs	https://doi.org/10.1021/acs.orglett.2c00313
Publication status	Published - 18 Mar 2022

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Chen, J. F., Tian, G., Liu, K., Zhang, N., Wang, N., Yin, X., & Chen, P. (2022). Pillar[5]arene-based Neutral Radicals with Doublet Red Emissions and Stable Chiroptical Properties. Organic Letters, 24(10), 1935-1940. https://doi.org/10.1021/acs.orglett.2c00313

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abstract = "Stable organic radicals with unique luminescence show great importance in photoelectromagnetic materials. We herein report two unusual radical-based systems (P5N-TTM and P5B-TTM) using the concerted effects of planar chiral pillar[5]arenes and tris(2,4,6-trichlorophenyl)methyl (TTM) radicals. The steric effect and electronic doublet-spin character of these radicals allowed the optical resolution and the first red emissions (∼650 nm) for pillar[5]arene derivatives. Notably, cross-coupling with macrocyclic pillar[5]arene, in turn, considerably enhanced the configurational stability of TTM radicals.",

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AU - Zhang, Niu

AU - Wang, Nan

AU - Yin, Xiaodong

AU - Chen, Pangkuan

PY - 2022/3/18

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N2 - Stable organic radicals with unique luminescence show great importance in photoelectromagnetic materials. We herein report two unusual radical-based systems (P5N-TTM and P5B-TTM) using the concerted effects of planar chiral pillar[5]arenes and tris(2,4,6-trichlorophenyl)methyl (TTM) radicals. The steric effect and electronic doublet-spin character of these radicals allowed the optical resolution and the first red emissions (∼650 nm) for pillar[5]arene derivatives. Notably, cross-coupling with macrocyclic pillar[5]arene, in turn, considerably enhanced the configurational stability of TTM radicals.

AB - Stable organic radicals with unique luminescence show great importance in photoelectromagnetic materials. We herein report two unusual radical-based systems (P5N-TTM and P5B-TTM) using the concerted effects of planar chiral pillar[5]arenes and tris(2,4,6-trichlorophenyl)methyl (TTM) radicals. The steric effect and electronic doublet-spin character of these radicals allowed the optical resolution and the first red emissions (∼650 nm) for pillar[5]arene derivatives. Notably, cross-coupling with macrocyclic pillar[5]arene, in turn, considerably enhanced the configurational stability of TTM radicals.

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Pillar[5]arene-based Neutral Radicals with Doublet Red Emissions and Stable Chiroptical Properties

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