Photosensitized Activation of Diazonium Derivatives for C-B Bond Formation.

Cage Escape Catalysis Diazonium Electron Transfer Hammett Mechanism Photo-induced Photoredox Transient

Journal

Chem catalysis
ISSN: 2667-1093
Titre abrégé: Chem Catal
Pays: Netherlands
ID NLM: 101776366

Informations de publication

Date de publication:
16 Feb 2023
Historique:
pmc-release: 16 02 2024
entrez: 20 3 2023
pubmed: 21 3 2023
medline: 21 3 2023
Statut: ppublish

Résumé

Aryl diazonium salts are ubiquitous building blocks in chemistry, as they are useful radical precursors in organic synthesis as well as for the functionalization of solid materials. They can be reduced electrochemically or through a photo-induced electron transfer reaction. Here we provide a detailed picture of the ground and excited-state reactivity of a series of 9 rare and earth abundant photosensitizers with 13 aryl diazonium salts, which also included 3 macrocyclic calix[4]arene tetradiazonium salts. Nanosecond transient absorption spectroscopy confirmed the occurrence of excited-state electron transfer and was used to quantify cage-escape yields,

Identifiants

pubmed: 36936750
doi: 10.1016/j.checat.2022.100490
pmc: PMC10022585
mid: NIHMS1859646
pii:
doi:

Types de publication

Journal Article

Langues

eng

Subventions

Organisme : NIGMS NIH HHS
ID : R01 GM102604
Pays : United States

Déclaration de conflit d'intérêts

DECLARATION OF INTERESTS The authors declare no competing interests.

Références

Photochem Photobiol Sci. 2022 Aug;21(8):1433-1444
pubmed: 35595935
J Phys Chem A. 2021 Oct 28;125(42):9355-9367
pubmed: 34665634
J Am Chem Soc. 2017 Sep 20;139(37):12903-12906
pubmed: 28853874
Photochem Photobiol Sci. 2012 Apr;11(4):632-6
pubmed: 22246402
J Am Chem Soc. 2011 Nov 23;133(46):18566-9
pubmed: 22047138
J Am Chem Soc. 2020 May 13;142(19):8565-8569
pubmed: 32307993
J Chem Phys. 2020 May 14;152(18):184102
pubmed: 32414274
Science. 2019 Jan 18;363(6424):249-253
pubmed: 30498167
Chem Sci. 2022 Jul 20;13(32):9165-9175
pubmed: 36093023
J Am Chem Soc. 2020 Apr 15;142(15):6847-6851
pubmed: 32216315
Org Biomol Chem. 2020 May 20;18(19):3624-3637
pubmed: 32154553
J Am Chem Soc. 2012 Feb 15;134(6):2958-61
pubmed: 22296099
Org Biomol Chem. 2013 Feb 13;11(10):1582-93
pubmed: 23358692
Chem Soc Rev. 2005 May;34(5):429-39
pubmed: 15852155
Inorg Chem. 2022 Nov 7;61(44):17515-17526
pubmed: 36279568
Inorg Chem. 2013 Oct 21;52(20):12140-51
pubmed: 24083360
Phys Rev B Condens Matter. 1988 Jan 15;37(2):785-789
pubmed: 9944570
Chemistry. 2021 Jun 16;27(34):8704-8708
pubmed: 33826178
J Am Chem Soc. 2020 Mar 25;142(12):5549-5555
pubmed: 32148029
Inorg Chem. 2002 Jun 17;41(12):3313-22
pubmed: 12055011
Chem Rev. 2021 May 26;121(10):5741-5829
pubmed: 33836126
Chem Commun (Camb). 2016 Aug 18;52(69):10493-6
pubmed: 27452314
Inorg Chem. 2019 Dec 16;58(24):16510-16517
pubmed: 31755267
Angew Chem Int Ed Engl. 2013 Apr 26;52(18):4734-43
pubmed: 23576379
Chemistry. 2018 Apr 25;24(24):6464-6472
pubmed: 29470842
J Am Chem Soc. 2021 Sep 29;143(38):15661-15673
pubmed: 34529421
Inorg Chem. 2007 May 14;46(10):3792-4
pubmed: 17425307
J Phys Chem A. 2014 Nov 13;118(45):10391-9
pubmed: 24910889
Phys Rev A Gen Phys. 1988 Sep 15;38(6):3098-3100
pubmed: 9900728
Chem Sci. 2021 Jul 1;12(29):9922-9933
pubmed: 34349964
Nat Commun. 2012;3:1130
pubmed: 23072800
Chem Soc Rev. 2011 Jul;40(7):3995-4048
pubmed: 21503288
J Am Chem Soc. 2021 Nov 24;143(46):19389-19398
pubmed: 34756036
Inorg Chem. 1996 Oct 23;35(22):6406-6412
pubmed: 11666787
J Phys Chem B. 2013 Aug 22;117(33):9669-76
pubmed: 23869464
J Am Chem Soc. 2022 Aug 10;144(31):14181-14194
pubmed: 35913126
Phys Chem Chem Phys. 2012 Oct 28;14(40):13731-45
pubmed: 22842806
Chem Rev. 2013 Jul 10;113(7):5322-63
pubmed: 23509883
Angew Chem Int Ed Engl. 2013 Jan 2;52(1):419-23
pubmed: 23047871
J Phys Chem A. 2014 Nov 13;118(45):10400-6
pubmed: 24882233
J Am Chem Soc. 2007 Feb 21;129(7):2147-60
pubmed: 17256860
J Am Chem Soc. 2020 Feb 12;142(6):2732-2737
pubmed: 31939663

Auteurs

Alexia Ripak (A)

Université catholique de Louvain (UCLouvain), Institut de la Matière Condensée et des Nanosciences (IMCN), Molecular Chemistry, Materials and Catalysis (MOST), Place Louis Pasteur 1, bte L4.01.02, 1348 Louvain-la-Neuve, Belgium.

Simon De Kreijger (S)

Université catholique de Louvain (UCLouvain), Institut de la Matière Condensée et des Nanosciences (IMCN), Molecular Chemistry, Materials and Catalysis (MOST), Place Louis Pasteur 1, bte L4.01.02, 1348 Louvain-la-Neuve, Belgium.

Renato N Sampaio (RN)

Department of Chemistry, University of North Carolina at Chapel Hill, Chapel Hill, North Carolina, 27599-3290, United States.

Cooper A Vincent (CA)

Department of Biochemistry, The University of Texas Southwestern Medical Center, 5323 Harry Hines Boulevard, Dallas, Texas 75390-9038, United States.

Émilie Cauët (É)

Spectroscopy, Quantum Chemistry and Atmospheric Remote Sensing (CP 160/09), Université libre de Bruxelles (ULB), 50 av. F. D. Roosevelt, CP160/09, B-1050 Brussels, Belgium.

Ivan Jabin (I)

Laboratoire de Chimie Organique, Université libre de Bruxelles (ULB), Avenue F. D. Roosevelt 50, CP160/06, B-1050 Brussels, Belgium.

Uttam K Tambar (UK)

Department of Biochemistry, The University of Texas Southwestern Medical Center, 5323 Harry Hines Boulevard, Dallas, Texas 75390-9038, United States.

Benjamin Elias (B)

Université catholique de Louvain (UCLouvain), Institut de la Matière Condensée et des Nanosciences (IMCN), Molecular Chemistry, Materials and Catalysis (MOST), Place Louis Pasteur 1, bte L4.01.02, 1348 Louvain-la-Neuve, Belgium.

Ludovic Troian-Gautier (L)

Université catholique de Louvain (UCLouvain), Institut de la Matière Condensée et des Nanosciences (IMCN), Molecular Chemistry, Materials and Catalysis (MOST), Place Louis Pasteur 1, bte L4.01.02, 1348 Louvain-la-Neuve, Belgium.
Lead contact.

Classifications MeSH