A Porphyrin-Based Covalent Organic Framework As Metal-Free Visible-LED-Light Photocatalyst for One-Pot Tandem Benzyl Alcohol Oxidation/Knoevenagel Condensation

Overview

Journal Nanomaterials (Basel)

Date 2023 Feb 11

PMID 36770519

Authors

Sara Oudi

Ali Reza Oveisi

Saba Daliran

Mostafa Khajeh

Amarajothi Dhakshinamoorthy

Hermenegildo Garcia

Affiliations

Soon will be listed here.

Abstract

A porphyrin-based covalent organic framework (COF), namely Porph-UOZ-COF (UOZ stands for the University of Zabol), has been designed and prepared via the condensation reaction of 5,10,15,20-tetrakis-(3,4-dihydroxyphenyl)porphyrin (DHPP) with 1,4-benzenediboronic acid (DBBA), under the solvothermal condition. The solid was characterized by spectroscopic, microscopic, and powder X-ray diffraction techniques. The resultant multifunctional COF revealed an outstanding performance in catalyzing a one-pot tandem selective benzylic C-H photooxygenation/Knoevenagel condensation reaction in the absence of additives or metals under visible-LED-light irradiation. Notably, the catalytic activity of the COF was superior to individual organic counterparts and the COF was both stable and reusable for four consecutive runs. The present approach illustrates the potential of COFs as promising metal-free (photo) catalysts for the development of tandem reactions.

Citing Articles

A Ru-Based Complex for Sustainable One-Pot Tandem Aerobic Oxidation-Knoevenagel Condensation Reactions.

Arafa W, Nayl A, Ahmed I, Youssef A, Mourad A, Brase S Molecules. 2024; 29(21).

PMID: 39519755 PMC: 11547704. DOI: 10.3390/molecules29215114.

References

Deng X, Li Z, Garcia H . Visible Light Induced Organic Transformations Using Metal-Organic-Frameworks (MOFs). Chemistry. 2017; 23(47):11189-11209. DOI: 10.1002/chem.201701460. View

Daliran S, Oveisi A, Peng Y, Lopez-Magano A, Khajeh M, Mas-Balleste R . Metal-organic framework (MOF)-, covalent-organic framework (COF)-, and porous-organic polymers (POP)-catalyzed selective C-H bond activation and functionalization reactions. Chem Soc Rev. 2022; 51(18):7810-7882. DOI: 10.1039/d1cs00976a. View

Pacholak P, Gontarczyk K, Kaminski R, Durka K, Lulinski S . Boronate Covalent and Hybrid Organic Frameworks Featuring P and P=O Lewis Base Sites. Chemistry. 2020; 26(56):12758-12768. PMC: 7589431. DOI: 10.1002/chem.202001960. View

Sarno D, Matienzo L, Jones Jr W . X-ray photoelectron spectroscopy as a probe of intermolecular interactions in porphyrin polymer thin films. Inorg Chem. 2001; 40(24):6308-15. DOI: 10.1021/ic010315v. View

Weiss J, Bryce D . A solid-state (11)b NMR and computational study of boron electric field gradient and chemical shift tensors in boronic acids and boronic esters. J Phys Chem A. 2010; 114(15):5119-31. PMC: 2857870. DOI: 10.1021/jp101416k. View

Miao Z, Luan Y, Qi C, Ramella D . The synthesis of a bifunctional copper metal organic framework and its application in the aerobic oxidation/Knoevenagel condensation sequential reaction. Dalton Trans. 2016; 45(35):13917-24. DOI: 10.1039/c6dt01690a. View

Sun J, Abednatanzi S, Chen H, Liu Y, Leus K, Van Der Voort P . Bifunctional Noble-Metal-Free Catalyst for the Selective Aerobic Oxidation-Knoevenagel One-Pot Reaction: Encapsulation of Polyoxometalates into an Alkylamine-Modified MIL-101 Framework. ACS Appl Mater Interfaces. 2021; 13(20):23558-23566. DOI: 10.1021/acsami.1c01621. View

Wang X, Sun Y, Xiao Y, Chen X, Huang X, Zhou H . Facile Solution-Refluxing Synthesis and Photocatalytic Dye Degradation of a Dynamic Covalent Organic Framework. Molecules. 2022; 27(22). PMC: 9697432. DOI: 10.3390/molecules27228002. View

Shing K, Cao B, Liu Y, Lee H, Li M, Lee Phillips D . Arylruthenium(III) Porphyrin-Catalyzed C-H Oxidation and Epoxidation at Room Temperature and [Ru(Por)(O)(Ph)] Intermediate by Spectroscopic Analysis and Density Functional Theory Calculations. J Am Chem Soc. 2018; 140(22):7032-7042. DOI: 10.1021/jacs.8b04470. View

10.

Schlachter A, Asselin P, Harvey P . Porphyrin-Containing MOFs and COFs as Heterogeneous Photosensitizers for Singlet Oxygen-Based Antimicrobial Nanodevices. ACS Appl Mater Interfaces. 2021; 13(23):26651-26672. DOI: 10.1021/acsami.1c05234. View

11.

Lin G, Ding H, Chen R, Peng Z, Wang B, Wang C . 3D Porphyrin-Based Covalent Organic Frameworks. J Am Chem Soc. 2017; 139(25):8705-8709. DOI: 10.1021/jacs.7b04141. View

12.

Wang J, Jin F, Ma H, Li X, Liu M, Kan J . Au@Cu(II)-MOF: Highly Efficient Bifunctional Heterogeneous Catalyst for Successive Oxidation-Condensation Reactions. Inorg Chem. 2016; 55(13):6685-91. DOI: 10.1021/acs.inorgchem.6b00925. View

13.

Dhakshinamoorthy A, Garcia H . Cascade reactions catalyzed by metal organic frameworks. ChemSusChem. 2014; 7(9):2392-410. DOI: 10.1002/cssc.201402148. View

14.

Shee N, Kim H . Sn(IV)-Porphyrin-Based Nanostructures Featuring Pd(II)-Mediated Supramolecular Arrays and Their Photocatalytic Degradation of Acid Orange 7 Dye. Int J Mol Sci. 2022; 23(22). PMC: 9696627. DOI: 10.3390/ijms232213702. View

15.

Guo J, Jiang D . Covalent Organic Frameworks for Heterogeneous Catalysis: Principle, Current Status, and Challenges. ACS Cent Sci. 2020; 6(6):869-879. PMC: 7318070. DOI: 10.1021/acscentsci.0c00463. View

16.

Zhang Y, Xu X, Liao Q, Wang Q, Han Q, Chen P . New potential of boron-based COFs: the biocompatible COF-1 for reactive oxygen generation and antimicrobial applications. J Mater Chem B. 2022; 10(17):3285-3292. DOI: 10.1039/d1tb02808a. View

17.

El-Kaderi H, Hunt J, Mendoza-Cortes J, Cote A, Taylor R, OKeeffe M . Designed synthesis of 3D covalent organic frameworks. Science. 2007; 316(5822):268-72. DOI: 10.1126/science.1139915. View

18.

Cote A, Benin A, Ockwig N, OKeeffe M, Matzger A, Yaghi O . Porous, crystalline, covalent organic frameworks. Science. 2005; 310(5751):1166-70. DOI: 10.1126/science.1120411. View

19.

Spitaleri L, Gangemi C, Purrello R, Nicotra G, Trusso Sfrazzetto G, Casella G . Covalently Conjugated Gold-Porphyrin Nanostructures. Nanomaterials (Basel). 2020; 10(9). PMC: 7558707. DOI: 10.3390/nano10091644. View

20.

Murase T, Nishijima Y, Fujita M . Cage-catalyzed Knoevenagel condensation under neutral conditions in water. J Am Chem Soc. 2011; 134(1):162-4. DOI: 10.1021/ja210068f. View