Enantiopure nanohoops through racemic resolution of diketo[


Journal

Chemical science
ISSN: 2041-6520
Titre abrégé: Chem Sci
Pays: England
ID NLM: 101545951

Informations de publication

Date de publication:
04 Aug 2021
Historique:
received: 18 05 2021
accepted: 19 06 2021
entrez: 11 8 2021
pubmed: 12 8 2021
medline: 12 8 2021
Statut: epublish

Résumé

Strained conjugated nanohoops are attractive synthetic targets due to the bending of their π-system, which leads to intriguing optoelectronic properties, among others. By incorporating non-mirror-symmetric aromatic panels, chiral nanohoops can be obtained. We herein present a strategy to enantiopure nanohoops by racemic resolution through chiral derivatization of diketone-embedded hoops. The resulting diketo[

Identifiants

pubmed: 34377404
doi: 10.1039/d1sc02718b
pii: d1sc02718b
pmc: PMC8336472
doi:

Types de publication

Journal Article

Langues

eng

Pagination

10150-10158

Informations de copyright

This journal is © The Royal Society of Chemistry.

Déclaration de conflit d'intérêts

There are no conflicts to declare.

Références

Science. 2019 Jul 19;365(6450):272-276
pubmed: 31320538
J Org Chem. 2020 Apr 3;85(7):5048-5057
pubmed: 32180403
J Chem Phys. 2015 Aug 7;143(5):054107
pubmed: 26254642
Angew Chem Int Ed Engl. 2009;48(33):6112-6
pubmed: 19588479
J Am Chem Soc. 2019 May 8;141(18):7421-7427
pubmed: 30998349
J Am Chem Soc. 1996 Jul 3;118(26):6317-6318
pubmed: 28872872
ACS Cent Sci. 2016 Oct 26;2(10):740-747
pubmed: 27800557
Chem Sci. 2019 Feb 25;10(13):3786-3790
pubmed: 30996967
Chem Sci. 2020 Mar 23;11(15):3923-3930
pubmed: 34122862
Angew Chem Int Ed Engl. 2020 Jan 7;59(2):559-573
pubmed: 31190449
Beilstein J Nanotechnol. 2014 Aug 20;5:1320-33
pubmed: 25247115
J Org Chem. 2020 Jan 3;85(1):34-43
pubmed: 31187987
J Am Chem Soc. 2012 Aug 1;134(30):12442-5
pubmed: 22800512
Angew Chem Int Ed Engl. 2016 Apr 18;55(17):5136-58
pubmed: 26890967
Front Chem. 2019 Oct 09;7:668
pubmed: 31649920
Chemistry. 2015 Sep 21;21(39):13488-500
pubmed: 26136234
Chem Commun (Camb). 2016 Dec 22;53(2):348-351
pubmed: 27929152
Angew Chem Int Ed Engl. 2020 Jan 20;59(4):1619-1626
pubmed: 31710148
Phys Chem Chem Phys. 2019 Feb 6;21(6):3250-3263
pubmed: 30681696
Angew Chem Int Ed Engl. 2021 Jul 12;60(29):15743-15766
pubmed: 32902109
Chem Rev. 2006 Dec;106(12):5274-90
pubmed: 17165688
Chemistry. 2018 May 23;24(29):7374-7387
pubmed: 29528165
Angew Chem Int Ed Engl. 2013 Nov 18;52(47):12224-6
pubmed: 24127399
Chem Commun (Camb). 2013 Jul 7;49(53):5930-2
pubmed: 23715509
Chem Phys Lett. 2010 Jul 9;494(1-3):1-7
pubmed: 21224898
Angew Chem Int Ed Engl. 2017 Jul 24;56(31):9106-9110
pubmed: 28608471
J Am Chem Soc. 2008 Dec 31;130(52):17646-7
pubmed: 19055403
Nat Chem. 2021 Mar;13(3):209-211
pubmed: 33649561
J Org Chem. 2018 Jan 19;83(2):656-663
pubmed: 29231725
Acc Chem Res. 2009 Aug 18;42(8):1108-16
pubmed: 19469494
Chemistry. 2021 Mar 12;27(15):4964-4970
pubmed: 33443300
Angew Chem Int Ed Engl. 2019 May 6;58(19):6244-6249
pubmed: 30843633
Chem Rev. 2001 May;101(5):1385-419
pubmed: 11710226
Angew Chem Int Ed Engl. 2010 Oct 11;49(42):7728-32
pubmed: 20836110
Acc Chem Res. 2019 Oct 15;52(10):2760-2767
pubmed: 31517488
Angew Chem Int Ed Engl. 2021 May 3;60(19):10680-10689
pubmed: 33596338
J Org Chem. 2020 Apr 17;85(8):5158-5172
pubmed: 32189503
Chem Commun (Camb). 2021 Jan 26;57(6):745-748
pubmed: 33346282
Chem Sci. 2021 Apr 28;12(22):7858-7865
pubmed: 34168839
J Am Chem Soc. 2019 Sep 25;141(38):14955-14960
pubmed: 31418559
Chem Soc Rev. 2015 Sep 21;44(18):6401-10
pubmed: 25913289
J Am Chem Soc. 2020 May 27;142(21):9834-9842
pubmed: 32362122
Angew Chem Int Ed Engl. 2010;49(4):757-9
pubmed: 20014269

Auteurs

Daniel Wassy (D)

Institute for Organic Chemistry, University of Freiburg Albertstraße 21 79104 Freiburg Germany besser@oc.uni-freiburg.de https://www.esser-lab.uni-freiburg.de.

Mathias Hermann (M)

Institute for Organic Chemistry, University of Freiburg Albertstraße 21 79104 Freiburg Germany besser@oc.uni-freiburg.de https://www.esser-lab.uni-freiburg.de.

Jan S Wössner (JS)

Institute for Organic Chemistry, University of Freiburg Albertstraße 21 79104 Freiburg Germany besser@oc.uni-freiburg.de https://www.esser-lab.uni-freiburg.de.

Lucas Frédéric (L)

Université Paris-Saclay, CEA, INRAE, Département Médicaments et Technologies pour la Santé (DMTS), SCBM 91191 Gif-sur-Yvette France.

Grégory Pieters (G)

Université Paris-Saclay, CEA, INRAE, Département Médicaments et Technologies pour la Santé (DMTS), SCBM 91191 Gif-sur-Yvette France.

Birgit Esser (B)

Institute for Organic Chemistry, University of Freiburg Albertstraße 21 79104 Freiburg Germany besser@oc.uni-freiburg.de https://www.esser-lab.uni-freiburg.de.
Freiburg Materials Research Center, University of Freiburg Stefan-Meier-Str. 21 79104 Freiburg Germany.
Freiburg Center for Interactive Materials and Bioinspired Technologies, University of Freiburg Georges-Köhler-Allee 105 79110 Freiburg Germany.

Classifications MeSH