Multiple-Porphyrin Functionalized Hexabenzocoronenes.
Scholl oxidation
hexabenzocoronene
nanographene
nanostructures
porphyrinoids
Journal
Chemistry (Weinheim an der Bergstrasse, Germany)
ISSN: 1521-3765
Titre abrégé: Chemistry
Pays: Germany
ID NLM: 9513783
Informations de publication
Date de publication:
27 Nov 2019
27 Nov 2019
Historique:
received:
08
07
2019
pubmed:
21
8
2019
medline:
21
8
2019
entrez:
21
8
2019
Statut:
ppublish
Résumé
Porphyrin-hexabenzocoronene architectures serve as good model compounds to study light-harvesting systems. Herein, the synthesis of porphyrin functionalized hexa-peri-hexabenzocoronenes (HBCs), in which one or more porphyrins are covalently linked to a central HBC core, is presented. A series of hexaphenylbenzenes (HPBs) was prepared and reacted under oxidative coupling conditions. The transformation to the respective HBC derivatives worked well with mono- and tri-porphyrin-substituted HPBs. However, if more porphyrins are attached to the HPB core, Scholl oxidations are hampered or completely suppressed. Hence, a change of the synthetic strategy was necessary to first preform the HBC core, followed by the introduction of the porphyrins. All products were fully characterized, including, if possible, single-crystal XRD. UV/Vis absorption spectra of porphyrin-HBCs showed, depending on the number of porphyrins as well as with respect to the substitution pattern, variations in their spectral features with strong distortions of the porphyrins' B-band.
Identifiants
pubmed: 31429504
doi: 10.1002/chem.201903113
pmc: PMC6899994
doi:
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
15083-15090Subventions
Organisme : DFG
ID : 182849149 - SFB 953
Organisme : Diamond Light Source
ID : MT11397
Informations de copyright
© 2019 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA.
Références
J Org Chem. 2005 Jan 21;70(2):749-52
pubmed: 15651837
J Org Chem. 2018 May 4;83(9):5132-5137
pubmed: 29644858
Angew Chem Int Ed Engl. 2008;47(27):4993-6
pubmed: 18506860
Chem Commun (Camb). 2014 Nov 14;50(88):13533-6
pubmed: 25238068
Org Lett. 2009 Aug 6;11(15):3474-7
pubmed: 19594139
Chemistry. 2002 Jun 17;8(12):2668-78
pubmed: 12391643
Chem Sci. 2019 Jun 5;10(27):6642-6650
pubmed: 31367317
Chem Soc Rev. 2015 Sep 21;44(18):6616-43
pubmed: 26186682
Chemistry. 2006 Oct 10;12(29):7576-84
pubmed: 16927274
Chem Rev. 2016 Aug 24;116(16):9565-627
pubmed: 27498592
J Am Chem Soc. 2008 Nov 5;130(44):14368-9
pubmed: 18839942
J Org Chem. 2010 Jul 16;75(14):4748-60
pubmed: 20575516
Chemistry. 2014 Feb 3;20(6):1615-21
pubmed: 24402766
J Am Chem Soc. 2018 Apr 25;140(16):5352-5355
pubmed: 29638125
J Org Chem. 2006 Jul 7;71(14):5067-81
pubmed: 16808493
Angew Chem Int Ed Engl. 2018 May 14;57(20):5938-5942
pubmed: 29508521
Chemistry. 2016 Nov 14;22(47):16755-16759
pubmed: 27661059
Chem Rev. 2007 Mar;107(3):718-47
pubmed: 17291049
Acc Chem Res. 2018 Sep 18;51(9):2083-2092
pubmed: 30156831
J Am Chem Soc. 2006 Feb 15;128(6):1818-27
pubmed: 16464080
Angew Chem Int Ed Engl. 2014 Nov 3;53(45):12231-5
pubmed: 25244699
Angew Chem Int Ed Engl. 2020 Feb 17;59(8):2998-3027
pubmed: 31342599
J Phys Chem B. 2013 Sep 26;117(38):11299-308
pubmed: 23534929
J Am Chem Soc. 2003 May 14;125(19):5849-60
pubmed: 12733926
J Synchrotron Radiat. 2012 May;19(Pt 3):435-41
pubmed: 22514182
Angew Chem Int Ed Engl. 2004 Oct 11;43(40):5331-5
pubmed: 15468181
Angew Chem Int Ed Engl. 2008;47(27):5071-4
pubmed: 18512838
Chem Sci. 2017 Jan 1;8(1):189-199
pubmed: 28451165
Angew Chem Int Ed Engl. 2018 Aug 27;57(35):11233-11237
pubmed: 29984483
J Org Chem. 2019 Feb 1;84(3):1489-1499
pubmed: 30596243
J Phys Chem B. 2004 May 20;108(20):6130-43
pubmed: 18950092
Angew Chem Int Ed Engl. 2013 Sep 9;52(37):9728-32
pubmed: 23913359
J Am Chem Soc. 2005 Jun 1;127(21):7700-2
pubmed: 15913359
J Am Chem Soc. 2004 Nov 24;126(46):15002-3
pubmed: 15547977
Chemistry. 2017 Dec 14;23(70):17687-17691
pubmed: 29108109
Chem Sci. 2016 Jul 1;7(7):4059-4066
pubmed: 30155049
Angew Chem Int Ed Engl. 2013 Sep 16;52(38):9900-30
pubmed: 23852649
Chem Commun (Camb). 2013 May 25;49(42):4827-9
pubmed: 23595595
Chemistry. 2004 Mar 5;10(5):1227-38
pubmed: 15007812
J Am Chem Soc. 2011 Mar 9;133(9):2916-22
pubmed: 21314185
J Am Chem Soc. 2010 Feb 3;132(4):1410-23
pubmed: 20052981
Chem Commun (Camb). 2005 Dec 14;(46):5736-8
pubmed: 16307129
J Org Chem. 2007 Mar 30;72(7):2279-88
pubmed: 17326684
Angew Chem Int Ed Engl. 2019 Jun 24;58(26):8932-8937
pubmed: 30968516
Chemistry. 2011 Mar 28;17(14):3837-41
pubmed: 21416491
Chem Soc Rev. 2015 Feb 21;44(4):943-69
pubmed: 24480993
J Am Chem Soc. 2003 Aug 13;125(32):9668-81
pubmed: 12904033
Org Biomol Chem. 2007 Jun 7;5(11):1679-91
pubmed: 17520134
J Am Chem Soc. 2017 Aug 30;139(34):11779-11788
pubmed: 28749146
Chemistry. 2019 Nov 27;25(66):15083-15090
pubmed: 31429504
Chem Soc Rev. 2012 Jul 21;41(14):4808-26
pubmed: 22659941
J Am Chem Soc. 2004 Sep 15;126(36):11311-21
pubmed: 15355114
Chemistry. 2018 Oct 22;24(59):15818-15824
pubmed: 30151869