Discovery of an all-donor aromatic [2]catenane

Tiberiu M. Gianga; Edwige Audibert; Anamaria Trandafir; Gabriele Kociok-Köhn; G. Dan Pantoş

doi:10.1039/d0sc04317f

Discovery of an all-donor aromatic [2]catenane

Tiberiu M. Gianga, Edwige Audibert, Anamaria Trandafir, Gabriele Kociok-Köhn, G. Dan Pantoş

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15 Citations (SciVal)

Abstract

We report herein the first all-donor aromatic [2]catenane formed through dynamic combinatorial chemistry, using single component libraries. The building block is a benzo[1,2-b:4,5-b′]dithiophene derivative, a π-donor molecule, with cysteine appendages that allow for disulfide exchange. The hydrophobic effect plays an essential role in the formation of the all-donor [2]catenane. The design of the building block allows the formation of a quasi-fused pentacyclic core, which enhances the stacking interactions between the cores. The [2]catenane has chiro-optical and fluorescent properties, being also the first known DCC-disulphide-based interlocked molecule to be fluorescent.

Original language	English
Pages (from-to)	9685-9690
Number of pages	6
Journal	Chemical Science
Volume	11
Issue number	35
Early online date	24 Aug 2020
DOIs	https://doi.org/10.1039/d0sc04317f
Publication status	Published - 21 Sept 2020

Bibliographical note

Funding Information:
This work was funded by the EPSRC (DTA TMG, AT) and the University of Bath (AT). X-ray diffraction, NMR and HRMS facilities were provided through the Materials and Chemical Characterisation Facility (MC2), at the University of Bath.

Publisher Copyright:
© The Royal Society of Chemistry 2020.

Copyright:
Copyright 2020 Elsevier B.V., All rights reserved.

Funding

This work was funded by the EPSRC (DTA TMG, AT) and the University of Bath (AT). X-ray diffraction, NMR and HRMS facilities were provided through the Materials and Chemical Characterisation Facility (MC2), at the University of Bath.

ASJC Scopus subject areas

General Chemistry

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Cite this

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title = "Discovery of an all-donor aromatic [2]catenane",

abstract = "We report herein the first all-donor aromatic [2]catenane formed through dynamic combinatorial chemistry, using single component libraries. The building block is a benzo[1,2-b:4,5-b′]dithiophene derivative, a π-donor molecule, with cysteine appendages that allow for disulfide exchange. The hydrophobic effect plays an essential role in the formation of the all-donor [2]catenane. The design of the building block allows the formation of a quasi-fused pentacyclic core, which enhances the stacking interactions between the cores. The [2]catenane has chiro-optical and fluorescent properties, being also the first known DCC-disulphide-based interlocked molecule to be fluorescent.",

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AU - Trandafir, Anamaria

AU - Kociok-Köhn, Gabriele

AU - Pantoş, G. Dan

N1 - Funding Information: This work was funded by the EPSRC (DTA TMG, AT) and the University of Bath (AT). X-ray diffraction, NMR and HRMS facilities were provided through the Materials and Chemical Characterisation Facility (MC2), at the University of Bath. Publisher Copyright: © The Royal Society of Chemistry 2020. Copyright: Copyright 2020 Elsevier B.V., All rights reserved.

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N2 - We report herein the first all-donor aromatic [2]catenane formed through dynamic combinatorial chemistry, using single component libraries. The building block is a benzo[1,2-b:4,5-b′]dithiophene derivative, a π-donor molecule, with cysteine appendages that allow for disulfide exchange. The hydrophobic effect plays an essential role in the formation of the all-donor [2]catenane. The design of the building block allows the formation of a quasi-fused pentacyclic core, which enhances the stacking interactions between the cores. The [2]catenane has chiro-optical and fluorescent properties, being also the first known DCC-disulphide-based interlocked molecule to be fluorescent.

AB - We report herein the first all-donor aromatic [2]catenane formed through dynamic combinatorial chemistry, using single component libraries. The building block is a benzo[1,2-b:4,5-b′]dithiophene derivative, a π-donor molecule, with cysteine appendages that allow for disulfide exchange. The hydrophobic effect plays an essential role in the formation of the all-donor [2]catenane. The design of the building block allows the formation of a quasi-fused pentacyclic core, which enhances the stacking interactions between the cores. The [2]catenane has chiro-optical and fluorescent properties, being also the first known DCC-disulphide-based interlocked molecule to be fluorescent.

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ER -

Discovery of an all-donor aromatic [2]catenane

Abstract

Bibliographical note

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ASJC Scopus subject areas

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