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

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

12 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

Access to Document

10.1039/d0sc04317fLicence: CC BY

Cite this

@article{50c8584f3cad4b449874e67d98ad6e0a,

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.",

author = "Gianga, {Tiberiu M.} and Edwige Audibert and Anamaria Trandafir and Gabriele Kociok-K{\"o}hn and Panto{\c s}, {G. Dan}",

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: {\textcopyright} The Royal Society of Chemistry 2020. Copyright: Copyright 2020 Elsevier B.V., All rights reserved.",

year = "2020",

month = sep,

day = "21",

doi = "10.1039/d0sc04317f",

language = "English",

volume = "11",

pages = "9685--9690",

journal = "Chemical Science",

issn = "2041-6520",

publisher = "Royal Society of Chemistry",

number = "35",

}

TY - JOUR

T1 - Discovery of an all-donor aromatic [2]catenane

AU - Gianga, Tiberiu M.

AU - Audibert, Edwige

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.

PY - 2020/9/21

Y1 - 2020/9/21

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.

UR - http://www.scopus.com/inward/record.url?scp=85092243194&partnerID=8YFLogxK

U2 - 10.1039/d0sc04317f

DO - 10.1039/d0sc04317f

M3 - Article

AN - SCOPUS:85092243194

SN - 2041-6520

VL - 11

SP - 9685

EP - 9690

JO - Chemical Science

JF - Chemical Science

IS - 35

ER -

Discovery of an all-donor aromatic [2]catenane

Abstract

Bibliographical note

Funding

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this