Diagnosing Ring Current(s) in Figure-Eight Skeletons: A 3D Through-Space Conjugation in the Two-Loops Crossing.
Journal
Organic letters
ISSN: 1523-7052
Titre abrégé: Org Lett
Pays: United States
ID NLM: 100890393
Informations de publication
Date de publication:
15 Jul 2022
15 Jul 2022
Historique:
pubmed:
8
7
2022
medline:
8
7
2022
entrez:
7
7
2022
Statut:
ppublish
Résumé
The macrocyclic structures with local conjugation readily undergo a redox-triggered change in the diatropic character, leading to a global current-density pathway of the doubly charged systems. The figure-eight geometry of the neutral dimer does not significantly change upon oxidation according to the spectroscopic and computational data. The oxidation leads to 3D cross-conjugation at the intersection of the two ethylene bridges resulting in a global ring current.
Identifiants
pubmed: 35796415
doi: 10.1021/acs.orglett.2c01625
pmc: PMC9348834
doi:
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
4876-4880Références
J Phys Chem A. 2009 Jul 30;113(30):8668-76
pubmed: 19586004
Chem Commun (Camb). 2021 Nov 23;57(93):12362-12378
pubmed: 34726205
J Am Chem Soc. 2021 Oct 6;143(39):15924-15929
pubmed: 34550688
J Chem Phys. 2004 Sep 1;121(9):3952-63
pubmed: 15332941
Nature. 2017 Jan 12;541(7636):200-203
pubmed: 27992878
Nat Chem. 2020 Mar;12(3):236-241
pubmed: 31959963
Chem Rev. 2017 Feb 22;117(4):2584-2640
pubmed: 27537063
Nat Commun. 2016 Nov 30;7:13620
pubmed: 27901014
Chem Commun (Camb). 2019 Apr 11;55(31):4558-4561
pubmed: 30931464
Angew Chem Int Ed Engl. 2000 Mar;39(6):1101-1105
pubmed: 10760933
J Org Chem. 2016 Aug 5;81(15):6244-52
pubmed: 27398717
Chemistry. 2019 Dec 5;25(68):15477-15482
pubmed: 31535404
Chem Rev. 2005 Oct;105(10):3842-88
pubmed: 16218569
Nat Chem. 2020 Mar;12(3):242-248
pubmed: 31959959
Org Lett. 2021 Dec 17;23(24):9436-9440
pubmed: 34870434
Chem Rev. 2006 Dec;106(12):4820-42
pubmed: 17165676
Chemistry. 2001 Dec 3;7(23):5099-112
pubmed: 11775683
Chem Rev. 2005 Oct;105(10):3758-72
pubmed: 16218566
Org Lett. 2015 Jun 19;17(12):3090-3
pubmed: 26053127
J Org Chem. 2012 May 4;77(9):4288-97
pubmed: 22486367
J Am Chem Soc. 2021 Jul 21;143(28):10676-10685
pubmed: 34170675
Chem Asian J. 2015 Jul;10(7):1438-51
pubmed: 25779771
Angew Chem Int Ed Engl. 2019 Aug 19;58(34):11742-11746
pubmed: 31225671
J Am Chem Soc. 2022 Jan 19;144(2):862-871
pubmed: 34910487
J Org Chem. 2013 Sep 20;78(18):9505-11
pubmed: 23988162
J Org Chem. 2009 Sep 4;74(17):6495-502
pubmed: 19711991
Angew Chem Int Ed Engl. 2014 Mar 10;53(11):2992-6
pubmed: 24604815
Angew Chem Int Ed Engl. 2020 Jul 27;59(31):12958-12964
pubmed: 32368821
Nat Commun. 2019 Aug 8;10(1):3576
pubmed: 31395873
Chem Rev. 2001 May;101(5):1385-419
pubmed: 11710226
J Phys Chem Lett. 2018 Apr 5;9(7):1627-1632
pubmed: 29532659
Phys Chem Chem Phys. 2022 Jan 19;24(3):1666-1674
pubmed: 34981802
Chem Rev. 2005 Oct;105(10):3773-811
pubmed: 16218567
Angew Chem Int Ed Engl. 2021 Apr 12;60(16):9063-9070
pubmed: 33406296
Angew Chem Int Ed Engl. 2015 Feb 2;54(6):1906-9
pubmed: 25529929
Angew Chem Int Ed Engl. 2000 Mar;39(6):1105-1108
pubmed: 10760934
Org Lett. 2021 May 7;23(9):3652-3656
pubmed: 33856224