Porphyrin as a versatile visible-light-activatable organic/metal hybrid photoremovable protecting group.
Journal
Nature communications
ISSN: 2041-1723
Titre abrégé: Nat Commun
Pays: England
ID NLM: 101528555
Informations de publication
Date de publication:
24 06 2022
24 06 2022
Historique:
received:
11
08
2021
accepted:
03
06
2022
pubmed:
25
6
2022
medline:
29
6
2022
entrez:
24
6
2022
Statut:
epublish
Résumé
Photoremovable protecting groups (PPGs) represent one of the main contemporary implementations of photochemistry in diverse fields of research and practical applications. For the past half century, organic and metal-complex PPGs were considered mutually exclusive classes, each of which provided unique sets of physical and chemical properties thanks to their distinctive structures. Here, we introduce the meso-methylporphyrin group as a prototype hybrid-class PPG that unites traditionally exclusive elements of organic and metal-complex PPGs within a single structure. We show that the porphyrin scaffold allows extensive modularity by functional separation of the metal-binding chromophore and up to four sites of leaving group release. The insertion of metal ions can be used to tune their spectroscopic, photochemical, and biological properties. We provide a detailed description of the photoreaction mechanism studied by steady-state and transient absorption spectroscopies and quantum-chemical calculations. Our approach applied herein could facilitate access to a hitherto untapped chemical space of potential PPG scaffolds.
Identifiants
pubmed: 35750661
doi: 10.1038/s41467-022-31288-2
pii: 10.1038/s41467-022-31288-2
pmc: PMC9232598
doi:
Substances chimiques
Ions
0
Metals
0
Porphyrins
0
Types de publication
Journal Article
Research Support, Non-U.S. Gov't
Langues
eng
Sous-ensembles de citation
IM
Pagination
3614Informations de copyright
© 2022. The Author(s).
Références
J Chem Phys. 2005 Jan 15;122(3):34107
pubmed: 15740192
J Phys Chem B. 2013 Oct 31;117(43):13490-6
pubmed: 24144045
Dalton Trans. 2018 Aug 21;47(31):10330-10343
pubmed: 29978870
J Am Chem Soc. 2020 Mar 11;142(10):4671-4679
pubmed: 32037819
J Phys Chem A. 2020 Sep 24;124(38):7776-7794
pubmed: 32926787
Acc Chem Res. 2015 Dec 15;48(12):3064-72
pubmed: 26569596
Metallomics. 2014 Aug;6(8):1324-35
pubmed: 24850462
Angew Chem Int Ed Engl. 2017 Feb 6;56(7):1784-1788
pubmed: 28079953
Photochem Photobiol Sci. 2007 Sep;6(9):995-1002
pubmed: 17721599
J Phys Chem A. 2016 Dec 15;120(49):9719-9731
pubmed: 27973797
J Chem Theory Comput. 2020 Sep 8;16(9):5809-5820
pubmed: 32687703
J Control Release. 2019 Mar 28;298:154-176
pubmed: 30742854
Chem Commun (Camb). 2012 May 16;48(39):4770-2
pubmed: 22473460
J Am Chem Soc. 2017 Oct 25;139(42):15168-15175
pubmed: 29039200
Adv Healthc Mater. 2020 Apr;9(7):e1901553
pubmed: 32100475
Sci Rep. 2017 Dec 4;7(1):16865
pubmed: 29203809
Adv Healthc Mater. 2016 Feb 4;5(3):305-310
pubmed: 26639103
Sci Adv. 2020 Jan 17;6(3):eaay0065
pubmed: 32010768
J Photochem Photobiol A Chem. 2008 Dec 15;200(2-3):346-355
pubmed: 20016663
J Am Chem Soc. 2015 Mar 25;137(11):3783-6
pubmed: 25751156
J Org Chem. 1999 Apr 16;64(8):2864-2872
pubmed: 11674358
Chemistry. 2020 Dec 15;26(70):16666-16675
pubmed: 32585068
J Phys Chem A. 2008 Nov 6;112(44):11044-51
pubmed: 18855369
Chem Commun (Camb). 2015 Apr 14;51(29):6369-72
pubmed: 25761909
Chemphyschem. 2008 Feb 1;9(2):282-92
pubmed: 18189251
J Am Chem Soc. 2007 Apr 18;129(15):4747-61
pubmed: 17381092
J Comput Chem. 2016 May 5;37(12):1082-91
pubmed: 26786747
Angew Chem Int Ed Engl. 2020 Oct 12;59(42):18386-18389
pubmed: 32671906
J Phys Chem A. 2015 Feb 26;119(8):1267-78
pubmed: 25633537
Chem Rev. 2019 Jan 23;119(2):1138-1192
pubmed: 30299085
Photochem Photobiol Sci. 2002 Apr;1(4):283-7
pubmed: 12661969
Org Lett. 2017 May 19;19(10):2622-2625
pubmed: 28485152
Acta Crystallogr A. 2008 Jan;64(Pt 1):112-22
pubmed: 18156677
J Chem Phys. 2007 Mar 28;126(12):124101
pubmed: 17411102
Chem Rev. 2020 Dec 23;120(24):13135-13272
pubmed: 33125209
Science. 2009 Apr 3;324(5923):59-63
pubmed: 19342581
Acc Chem Res. 2020 Aug 18;53(8):1593-1604
pubmed: 32692149
ChemMedChem. 2007 Mar;2(3):360-5
pubmed: 17245681
J Org Chem. 2020 Mar 6;85(5):3527-3537
pubmed: 31977220
Chem Rev. 2013 Jan 9;113(1):119-91
pubmed: 23256727