A flavin-inspired covalent organic framework for photocatalytic alcohol oxidation.
Journal
Chemical science
ISSN: 2041-6520
Titre abrégé: Chem Sci
Pays: England
ID NLM: 101545951
Informations de publication
Date de publication:
24 Nov 2021
24 Nov 2021
Historique:
received:
28
07
2021
accepted:
02
11
2021
entrez:
15
12
2021
pubmed:
16
12
2021
medline:
16
12
2021
Statut:
epublish
Résumé
Covalent organic frameworks (COFs) offer a number of key properties that predestine them to be used as heterogeneous photocatalysts, including intrinsic porosity, long-range order, and light absorption. Since COFs can be constructed from a practically unlimited library of organic building blocks, these properties can be precisely tuned by choosing suitable linkers. Herein, we report the construction and use of a novel COF (FEAx-COF) photocatalyst, inspired by natural flavin cofactors. We show that the functionality of the alloxazine chromophore incorporated into the COF backbone is retained and study the effects of this heterogenization approach by comparison with similar molecular photocatalysts. We find that the integration of alloxazine chromophores into the framework significantly extends the absorption spectrum into the visible range, allowing for photocatalytic oxidation of benzylic alcohols to aldehydes even with low-energy visible light. In addition, the activity of the heterogeneous COF photocatalyst is less dependent on the chosen solvent, making it more versatile compared to molecular alloxazines. Finally, the use of oxygen as the terminal oxidant renders FEAx-COF a promising and "green" heterogeneous photocatalyst.
Identifiants
pubmed: 34909156
doi: 10.1039/d1sc04143f
pii: d1sc04143f
pmc: PMC8612393
doi:
Types de publication
Journal Article
Langues
eng
Pagination
15143-15150Informations de copyright
This journal is © The Royal Society of Chemistry.
Déclaration de conflit d'intérêts
There are no conflicts to declare.
Références
Nat Commun. 2015 Sep 30;6:8508
pubmed: 26419805
Chem Sci. 2019 Nov 21;11(2):543-550
pubmed: 32206271
Proc Natl Acad Sci U S A. 2017 Aug 29;114(35):9279-9283
pubmed: 28802257
J Org Chem. 2003 Jul 25;68(15):5890-6
pubmed: 12868923
Free Radic Biol Med. 2014 Dec;77:64-70
pubmed: 25236741
Nature. 1976 Sep 30;263(5576):442-3
pubmed: 972689
Chem Soc Rev. 2008 Mar;37(3):479-89
pubmed: 18224258
Org Lett. 2012 Mar 2;14(5):1314-7
pubmed: 22339088
Chem Commun (Camb). 2014 Dec 21;50(98):15480-98
pubmed: 25316254
Phys Chem Chem Phys. 2011 May 21;13(19):8869-80
pubmed: 21461426
Chemistry. 2008;14(6):1854-65
pubmed: 18058784
J Phys Chem A. 2016 Sep 22;120(37):7294-300
pubmed: 27565198
Annu Rev Biochem. 1980;49:695-726
pubmed: 6250449
Angew Chem Int Ed Engl. 2019 Jul 8;58(28):9443-9447
pubmed: 31090130
J Am Chem Soc. 1986 Nov 1;108(24):7773-8
pubmed: 22283285
Chem Commun (Camb). 2014 Jun 28;50(51):6688-99
pubmed: 24699920
Chem Soc Rev. 2013 Jan 7;42(1):97-113
pubmed: 22990664
J Am Chem Soc. 2020 Jan 8;142(1):16-20
pubmed: 31820958
Adv Sci (Weinh). 2021 Sep;8(18):e2100631
pubmed: 34339109
Chem Commun (Camb). 2015 Aug 4;51(60):12036-9
pubmed: 26121238
Chem Soc Rev. 2011 Jan;40(1):102-13
pubmed: 20532341
Phys Chem Chem Phys. 2016 Jul 21;18(27):18575-83
pubmed: 27346787
J Am Chem Soc. 2020 Nov 25;142(47):20107-20116
pubmed: 33185433
Chemistry. 2021 May 17;27(28):7738-7744
pubmed: 33788327
Chemistry. 2004 Dec 3;10(24):6224-31
pubmed: 15487030
Nature. 1976 Jul 29;262(5567):420-1
pubmed: 183131
J Chem Phys. 2010 Apr 21;132(15):154104
pubmed: 20423165
J Chem Theory Comput. 2015 Jan 13;11(1):132-8
pubmed: 26574211
J Am Chem Soc. 2004 Dec 15;126(49):15999-6006
pubmed: 15584734
Org Biomol Chem. 2018 Sep 19;16(36):6809-6817
pubmed: 30203820
J Am Chem Soc. 2003 Mar 12;125(10):2868-9
pubmed: 12617641
Biochem J. 1988 Jul 1;253(1):287-9
pubmed: 2844170
J Am Chem Soc. 2017 Feb 8;139(5):2035-2044
pubmed: 28103670
Angew Chem Int Ed Engl. 2019 May 6;58(19):6430-6434
pubmed: 30884054
Chem Commun (Camb). 2018 May 29;54(44):5606-5609
pubmed: 29767201
J Am Chem Soc. 2019 Jul 17;141(28):11082-11092
pubmed: 31260279
Chem Asian J. 2006 Jul 17;1(1-2):136-47
pubmed: 17441048
Chem Rev. 2017 Sep 13;117(17):11302-11336
pubmed: 28777548
Photochem Photobiol Sci. 2010 Oct 28;9(10):1367-77
pubmed: 20838686
Chemistry. 2013 Jan 14;19(3):1066-75
pubmed: 23197435
Org Biomol Chem. 2011 Nov 7;9(21):7318-26
pubmed: 21879132
J Am Chem Soc. 2014 Dec 24;136(51):17802-7
pubmed: 25412210
Mol Pharmacol. 1979 Sep;16(2):676-85
pubmed: 229403
Org Lett. 2010 Jan 1;12(1):32-5
pubmed: 19950976
ACS Energy Lett. 2018 Feb 9;3(2):400-409
pubmed: 29457140
Chem Rev. 2013 Jul 10;113(7):5322-63
pubmed: 23509883
Adv Mater. 2011 May 24;23(20):2367-71
pubmed: 21462372
Chem Sci. 2020 Jul 8;11(47):12647-12654
pubmed: 34094458
Angew Chem Int Ed Engl. 2015 Jan 19;54(4):1347-51
pubmed: 25470783
Angew Chem Int Ed Engl. 2017 Nov 20;56(47):15136-15140
pubmed: 29024307
Nat Chem. 2018 Dec;10(12):1180-1189
pubmed: 30275507