Diastereoselective formation of homochiral flexible perylene bisimide cyclophanes and their hybrids with fullerenes.
Journal
Chemical science
ISSN: 2041-6520
Titre abrégé: Chem Sci
Pays: England
ID NLM: 101545951
Informations de publication
Date de publication:
08 Dec 2021
08 Dec 2021
Historique:
received:
03
08
2021
accepted:
07
10
2021
entrez:
10
1
2022
pubmed:
11
1
2022
medline:
11
1
2022
Statut:
epublish
Résumé
Cyclophanes of different ring sizes featuring perylene-3,4:9,10-tetracarboxylic acid bisimide (PBI) linked by flexible malonates were designed, synthesized, and investigated with respect to their structural, chemical and photo-physical properties. It is predominantly the number of PBIs and their geometric arrangement, which influence dramatically their properties. For example, two-PBI containing cyclophanes reveal physico-chemical characteristics that are governed by strong co-facial π-π interactions. This is in stark contrast to cyclophanes with either three or four PBIs. Key to co-facial π-π stackings are the flexible malonate linkers, which, in turn, set up the ways and means for diastereoselectivity of the homochiral PBIs at low temperatures, on one hand. In terms of selectivity, diastereomeric (
Identifiants
pubmed: 35003577
doi: 10.1039/d1sc04242d
pii: d1sc04242d
pmc: PMC8653996
doi:
Types de publication
Journal Article
Langues
eng
Pagination
15491-15502Informations de copyright
This journal is © The Royal Society of Chemistry.
Déclaration de conflit d'intérêts
There are no conflicts to declare.
Références
Chem Commun (Camb). 2009 Jan 28;(4):419-21
pubmed: 19137171
ACS Nano. 2020 Jul 28;14(7):8266-8275
pubmed: 32579333
J Am Chem Soc. 2020 Jan 8;142(1):349-364
pubmed: 31778308
J Am Chem Soc. 2017 Feb 8;139(5):2014-2021
pubmed: 28080033
Chemistry. 2017 Jan 31;23(7):1667-1675
pubmed: 27943445
Chem Commun (Camb). 2009 May 7;(17):2245-69
pubmed: 19377656
Chemistry. 2009 Jul 27;15(30):7423-33
pubmed: 19551779
Chem Commun (Camb). 2004 Jul 21;(14):1564-79
pubmed: 15263926
Chemistry. 2008;14(23):7000-10
pubmed: 18604858
Angew Chem Int Ed Engl. 2020 Sep 21;59(39):17084-17090
pubmed: 32520408
J Org Chem. 2013 Dec 6;78(23):11962-9
pubmed: 24128112
J Am Chem Soc. 2008 Jul 2;130(26):8271-9
pubmed: 18540670
Angew Chem Int Ed Engl. 2015 Aug 24;54(35):10165-8
pubmed: 26079394
ACS Omega. 2020 Jul 15;5(29):18449-18457
pubmed: 32743222
Chemistry. 2018 Mar 26;24(18):4671-4679
pubmed: 29334163
Adv Mater. 2013 Jan 18;25(3):410-4
pubmed: 22807177
Chemistry. 2018 Sep 20;24(53):14088-14100
pubmed: 30058727
Angew Chem Int Ed Engl. 2003 Jul 14;42(27):3158-62
pubmed: 12866106
Chem Soc Rev. 2009 Jun;38(6):1587-97
pubmed: 19587954
Chem Rev. 2016 Feb 10;116(3):962-1052
pubmed: 26270260
Chem Sci. 2016 Aug 1;7(8):5428-5434
pubmed: 30034681
Chemistry. 2009 Jul 27;15(30):7434-46
pubmed: 19551780
J Am Chem Soc. 2018 Aug 8;140(31):9986-9995
pubmed: 29992819
J Am Chem Soc. 2002 Jul 24;124(29):8530-1
pubmed: 12121085
J Phys Chem Lett. 2019 Apr 18;10(8):1919-1927
pubmed: 30892901
J Phys Chem Lett. 2020 Dec 17;11(24):10329-10339
pubmed: 33232151
Angew Chem Int Ed Engl. 2021 Jul 5;60(28):15323-15327
pubmed: 33909943
Angew Chem Int Ed Engl. 2019 Mar 11;58(11):3516-3520
pubmed: 30576044
J Am Chem Soc. 2006 Aug 30;128(34):11150-9
pubmed: 16925433