Evaluation of an Imine-Linked Polymer Organic Framework for Storage and Release of HS and NO

Overview

Journal Materials (Basel)

Publisher MDPI

Date 2023 Feb 25

PMID 36837282

Authors

Silvia Carvalho

Joao Pires

Cristina Moiteiro

Moises L Pinto

Affiliations

Soon will be listed here.

Abstract

Hydrogen sulfide (HS) and nitric oxide (NO) are especially known as toxic and polluting gases, yet they are also endogenously produced and play key roles in numerous biological processes. These two opposing aspects of the gases highlight the need for new types of materials to be developed in addition to the most common materials such as activated carbons and zeolites. Herein, a new imine-linked polymer organic framework was obtained using the inexpensive and easy-to-access reagents isophthalaldehyde and 2,4,6-triaminopyrimidine in good yield (64%) through the simple and catalyst-free Schiff-base reaction. The polymeric material has microporosity, an surface area of 51 m/g, and temperature stability up to 300 °C. The obtained 2,4,6-triaminopyrimidine imine-linked polymer organic material has a higher capacity to adsorb NO (1.6 mmol/g) than HS (0.97 mmol/g). Release studies in aqueous solution showed that HS has a faster release (3 h) from the material than NO, for which a steady release was observed for at least 5 h. This result is the first evaluation of the possibility of an imine-linked polymer organic framework being used in the therapeutic release of NO or HS.

References

Wei Z, Lu X, Wang W, Mele G, Jiang Z . Excellent removal performance of 4,4'-biphenyldicarboxaldehyde m-phenylenediamine Schiff base magnetic polymer towards phenanthrene and 9-phenanthrol: Experimental, modeling and DFT calculations studies. J Hazard Mater. 2022; 441:129920. DOI: 10.1016/j.jhazmat.2022.129920. View

Chang Z, Zhang D, Chen Q, Bu X . Microporous organic polymers for gas storage and separation applications. Phys Chem Chem Phys. 2013; 15(15):5430-42. DOI: 10.1039/c3cp50517k. View

Kim J, Kang D, Yun H, Kang M, Singh N, Kim J . Post-synthetic modifications in porous organic polymers for biomedical and related applications. Chem Soc Rev. 2021; 51(1):43-56. DOI: 10.1039/d1cs00804h. View

Lee J, Cooper A . Advances in Conjugated Microporous Polymers. Chem Rev. 2020; 120(4):2171-2214. PMC: 7145355. DOI: 10.1021/acs.chemrev.9b00399. View

Jung D, Chen Z, Alayoglu S, Mian M, Goetjen T, Idrees K . Postsynthetically Modified Polymers of Intrinsic Microporosity (PIMs) for Capturing Toxic Gases. ACS Appl Mater Interfaces. 2021; 13(8):10409-10415. DOI: 10.1021/acsami.0c21741. View

Pinto R, Fernandes A, Antunes F, Lin Z, Rocha J, Pires J . New generation of nitric oxide-releasing porous materials: Assessment of their potential to regulate biological functions. Nitric Oxide. 2019; 90:29-36. DOI: 10.1016/j.niox.2019.05.010. View

Pinto R, Carvalho S, Antunes F, Pires J, Pinto M . Emerging Nitric Oxide and Hydrogen Sulfide Releasing Carriers for Skin Wound Healing Therapy. ChemMedChem. 2021; 17(1):e202100429. DOI: 10.1002/cmdc.202100429. View

Zhang G, Hua B, Dey A, Ghosh M, Moosa B, Khashab N . Intrinsically Porous Molecular Materials (IPMs) for Natural Gas and Benzene Derivatives Separations. Acc Chem Res. 2020; 54(1):155-168. DOI: 10.1021/acs.accounts.0c00582. View

Pinto R, Wang S, Tavares S, Pires J, Antunes F, Vimont A . Tuning Cellular Biological Functions Through the Controlled Release of NO from a Porous Ti-MOF. Angew Chem Int Ed Engl. 2020; 59(13):5135-5143. DOI: 10.1002/anie.201913135. View

10.

Dey D, Murmu N, Banerjee P . Tailor-made synthesis of an melamine-based aminal hydrophobic polymer for selective adsorption of toxic organic pollutants: an initiative towards wastewater purification. RSC Adv. 2022; 9(13):7469-7478. PMC: 9061213. DOI: 10.1039/c9ra00453j. View

11.

Pinto R, Antunes F, Pires J, Graca V, Brandao P, Pinto M . Vitamin B metal-organic frameworks as potential delivery vehicles for therapeutic nitric oxide. Acta Biomater. 2017; 51:66-74. DOI: 10.1016/j.actbio.2017.01.039. View

12.

Mohan A, Al-Sayah M, Ahmed A, El-Kadri O . Triazine-based porous organic polymers for reversible capture of iodine and utilization in antibacterial application. Sci Rep. 2022; 12(1):2638. PMC: 8850422. DOI: 10.1038/s41598-022-06671-0. View

13.

Feng L, Wang K, Day G, Ryder M, Zhou H . Destruction of Metal-Organic Frameworks: Positive and Negative Aspects of Stability and Lability. Chem Rev. 2020; 120(23):13087-13133. DOI: 10.1021/acs.chemrev.0c00722. View

14.

Li Z . Quantification of hydrogen sulfide concentration using methylene blue and 5,5'-dithiobis(2-nitrobenzoic acid) methods in plants. Methods Enzymol. 2015; 554:101-10. DOI: 10.1016/bs.mie.2014.11.031. View

15.

Wang S, Li H, Huang H, Cao X, Chen X, Cao D . Porous organic polymers as a platform for sensing applications. Chem Soc Rev. 2022; 51(6):2031-2080. DOI: 10.1039/d2cs00059h. View

16.

McKeown N, Budd P . Polymers of intrinsic microporosity (PIMs): organic materials for membrane separations, heterogeneous catalysis and hydrogen storage. Chem Soc Rev. 2006; 35(8):675-83. DOI: 10.1039/b600349d. View

17.

Chaoui N, Trunk M, Dawson R, Schmidt J, Thomas A . Trends and challenges for microporous polymers. Chem Soc Rev. 2017; 46(11):3302-3321. DOI: 10.1039/c7cs00071e. View

18.

Liu Y, Bian C, Li Y, Sun P, Xiao Y, Xiao X . Aminobenzaldehyde convelently modified graphitic carbon nitride photocatalyst through Schiff base reaction: Regulating electronic structure and improving visible-light-driven photocatalytic activity for moxifloxacin degradation. J Colloid Interface Sci. 2022; 630(Pt A):867-878. DOI: 10.1016/j.jcis.2022.10.073. View

19.

Zacharia I, Deen W . Diffusivity and solubility of nitric oxide in water and saline. Ann Biomed Eng. 2005; 33(2):214-22. DOI: 10.1007/s10439-005-8980-9. View

20.

Batista M, Pinto M, Antunes F, Pires J, Carvalho S . Chitosan Biocomposites for the Adsorption and Release of HS. Materials (Basel). 2021; 14(21). PMC: 8587643. DOI: 10.3390/ma14216701. View