Molecular Möbius strips: twist for a bright future

Yao, Bin; Liu, Xingyan; Guo, Tingwang; Sun, Hongfei; Wang, Wei

doi:10.1039/d2qo00829g

Conformationally Locked Cyclo[2]Dipyrrins Linked with Anthracene Subunits: Synthesis and Chiroptical Properties

Gokulnath

¹

,

Nambiar

²

,

Nag

³

et al. 2023

Angewandte Chemie

1

0

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Herein, we report the synthesis of anthracene‐containing twisted cyclo[2]dipyrrin 1 by utilizing a non‐planar building block, 1,5‐dipyrrylanthracene (1,5‐DPA). The non‐planar nature of the macrocycle enhanced the solubility and helped in structural characterization. Macrocycle 1 adopts a twisted ‘figure of eight’ conformation stabilized by strong intramolecular H‐bonding interactions and exists as a pair of helical enantiomers, as revealed by X‐ray crystallographic analysis. More importantly, the sterically locked structure enabled facile optical resolution using chiral HPLC. The (P,P) and (M,M) enantiomers show moderate chiroptical properties, such as absorption dissymmetry factors |gabs| in the order of 10−3, and luminescence dissymmetry factors |glum| of 3.8×10−3 and 2.9×10−3 at 702 nm, respectively.

show abstract

Conformationally Locked Cyclo[2]Dipyrrins Linked with Anthracene Subunits: Synthesis and Chiroptical Properties

Gokulnath

¹

,

Nambiar

²

,

Nag

³

et al. 2023

View full text Add to dashboard Cite

Herein, we report the synthesis of anthracene‐containing twisted cyclo[2]dipyrrin 1 by utilizing a non‐planar building block, 1,5‐dipyrrylanthracene (1,5‐DPA). The non‐planar nature of the macrocycle enhanced the solubility and helped in structural characterization. Macrocycle 1 adopts a twisted ‘figure of eight’ conformation stabilized by strong intramolecular H‐bonding interactions and exists as a pair of helical enantiomers, as revealed by X‐ray crystallographic analysis. More importantly, the sterically locked structure enabled facile optical resolution using chiral HPLC. The (P,P) and (M,M) enantiomers show moderate chiroptical properties, such as absorption dissymmetry factors |gabs| in the order of 10−3, and luminescence dissymmetry factors |glum| of 3.8×10−3 and 2.9×10−3 at 702 nm, respectively.

show abstract

Theoretical investigation on optical properties of Möbius carbon nanobelts in one- and two-photon absorption

Yang

¹

,

Chen

²

,

Li

³

et al. 2023

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Molecular Möbius strips: twist for a bright future

Abstract: Attributed to their unique structural features and associated intriguing properties, molecular Möbius strips have attracted considerable attention. However, the precise synthesis of such attractive molecules remains a great challenge. Recently,...

Cited by 5 publications

References 60 publications

Conformationally Locked Cyclo[2]Dipyrrins Linked with Anthracene Subunits: Synthesis and Chiroptical Properties

Conformationally Locked Cyclo[2]Dipyrrins Linked with Anthracene Subunits: Synthesis and Chiroptical Properties

Conformationally Locked Cyclo[2]Dipyrrins Linked with Anthracene Subunits: Synthesis and Chiroptical Properties

Theoretical investigation on optical properties of Möbius carbon nanobelts in one- and two-photon absorption

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