TRUXENONE AND ISOTRUXENONE-BASED POROUS ORGANIC POLYMERS AS METAL-FREE, HETEROGENEOUS PHOTOCATALYSTS FOR VISIBLE-LIGHT-PROMOTED REDUCTION OF LUNG CANCER A549 CELLS

Authors

  • YongLi Tan (Corresponding Author) The Affiliated Changsha Central Hospital, Hengyang Medical School, University of South China, Changsha 410004, Hunan, China.
  • YeMu Zhu The Affiliated Changsha Central Hospital, Hengyang Medical School, University of South China, Changsha 410004, Hunan, China.
  • HaiFeng Duan The Affiliated Changsha Central Hospital, Hengyang Medical School, University of South China, Changsha 410004, Hunan, China.

Keywords:

A549 cells, Heterogeneous photocatalysis, Metal-Free, Porous polymers, Visible-Light

Abstract

While porous materials have been widely employed in numerous fields ranging from gas adsorption and separations, light emittance, sensing to energy storage, their applications in reducing respiratory morbidity are limited. In particular, the products obtained in a controlled manner using porous materials and thus applied to limit lung cancer cells multiplication are very rare. Here we report the synthesis of two new truxenone and isotruxenone-based porous organic polymers (POPs) via Friedel-Crafts alkylation/oxidation starting from truxene and isotruxene. These networks are thermally and chemically stable, and demonstrated as the first metal-free, heterogeneous photocatalysts for visible-light-induced tunable benzylic functionalization. Moreover, both POPs can be easily recovered and reused for at least 15 times without any apparent decrease in their photocatalytic activity. The synthetic utility of this newly-developed methodology is demonstrated in the value-added functionalization of chemical feedstocks such as xylenes and mesitylene, the resulting product can be used to reduce the number of lung cancer A549 cells.

References

[1] Yoon T.P., Ischay M.A., Du J. Visible Light Photocatalysis as a Greener Approach to Photochemical Synthesis. Nat. Chem. 2010, 2(7): 527-532. DOI: https://doi.org/10.1038/nchem.687.

[2] Xuan J., Xiao W.J. Visible-Light Photoredox Catalysis. Angew. Chem. Int. Ed. 2012, 51(28): 6828-6838. DOI: https://doi.org/10.1002/anie.201200223.

[3] Prier C.K., Rankic D.A., MacMillan D.W.C. Visible Light Photoredox Catalysis with Transition Metal Complexes: Applications in Organic Synthesis. Chem. Rev. 2013, 113(7): 5322-5363. DOI: https://doi.org/10.1021/cr300503r.

[4] Romero N.A., Nicewicz D.A. Organic Photoredox Catalysis. Chem Rev. 2016, 116(17): 10075-10166. DOI: https://doi.org/ 10.1021/acs.chemrev.6b00057.

[5] Xu Z.-Y., Luo Y., Wang H., Zhang D.-W., Li Z.-T. Porous Organic Polymers as Heterogeneous Catalysts for Visible Light-Induced Organic Transformations. Chin. J. Org. Chem. 2020, 40(11): 3777-3793. DOI: https://doi.org/10.6023/cjoc202003070.

[6] Wang T.-X., Liang H.-P., Anito D.A., Ding X., Han B.-H. Emerging Applications of Porous Organic Polymers in Visible-Light Photocatalysis. J. Mater. Chem. A. 2020, 8(15): 7003-7034. DOI: https://doi.org/10.1039/D0TA00364F.

[7] Zhang T., Xing G., Chen W., Chen L.. Porous Organic Polymers: A Promising Platform for Efficient Photocatalysis. Mater. Chem. Front. 2020, 4(2): 332-353. DOI: https://doi.org/10.1039/C9QM00633H.

[8] Ferguson C.T.J., Zhang K.A.I. Classical Polymers as Highly Tunable and Designable Heterogeneous Photocatalysts. ACS Catal. 2021, 11(15): 9547-9560. DOI: https://doi.org/10.1021/acscatal.1c02056.

[9] Liang H.-P., Chen Q., Han B.-H. Cationic Polycarbazole Networks as Visible-Light Heterogeneous Photocatalysts for Oxidative Organic Transformations. ACS Catal. 2018, 8(6): 5313-5322. DOI: https://doi.org/10.1021/acscatal.7b04494.

[10] Luo J., Lu J., Zhang J. Carbazole-Triazine Based Donor-Acceptor Porous Organic Frameworks for Efficient Visible-Light Photocatalytic Aerobic Oxidation Reactions. J. Mater. Chem. A. 2018, 6(31): 15154-15161. DOI: https://doi.org/10.1039/c8ta05329d.

[11] Li X., Ma X., Zhang F., Dong X., Lang X. Selective photocatalytic formation of sulfoxides by aerobic oxidation of sulfides over conjugated microporous polymers with thiazolo[5,4?d] thiazole linkage. Appl. Catal. B: Environ. 2021, 298: 120514-120623. DOI: https://doi.org/10.1016/j.apcatb.2021.120514.

[12] Hao H., Zhang F., Dong X., Lang X. 2D sp2 carbon-conjugated triazine covalent organic framework photocatalysis for blue light-induced selective oxidation of sulfides with O2. Appl. Catal. B: Environ. 2021, 299: 120691-120702. DOI: https://doi.org/10.1016/j.apcatb.2021.120691.

[13] Wang Z.J., Ghasimi S., Landfester K., Zhang K.A.I. Molecular Structural Design of Conjugated Microporous Poly(Benzooxadiazole) Networks for Enhanced Photocatalytic Activity with Visible Light. Adv. Mater. 2015, 27(40): 6265-6270. DOI: https://doi.org/10.1002/adma.201502735.

[14] Battula V.R., Singh H., Kumar S., Bala I., Pal S.K., Kailasam, K. Natural Sunlight Driven Oxidative Homocoupling of Amines by a Truxene-Based Conjugated Microporous Polymer. ACS Catal. 2018, 8(8): 6751-6759. DOI: https://doi.org/10.1021/acscatal.8b00623.

[15] Xu H., Li X., Hao H., Dong X., Sheng W., Lang X. Designing fluorene-based conjugated microporous polymers for blue light-driven photocatalytic selective oxidation of amines with oxygen. Appl. Catal. B: Environ. 2021, 285: 119796-119806. DOI: https://doi.org/10.1016/j.apcatb.2020.119796.

[16] Wei P., Qi M., Wang Z., Ding S., Yu W., Liu Q., Wang L., Wang H., An W., Wang W. Benzoxazole-Linked Ultrastable Covalent Organic Frameworks for Photocatalysis. J. Am. Chem. Soc. 2018, 140(13): 4623-4631. DOI: https://doi.org/10.1021/jacs.8b00571.

[17] Xu Z.-Y., Luo Y., Zhang D.-W., Wang H., Sun X.-W., Li Z.-T. Iridium complex-linked porous organic polymers for recyclable, broad-scope photocatalysis of organic transformations. Green Chem. 2020, 22(1): 136-143. DOI: https://doi.org/10.1039/c9gc03688a.

[18] Nailwal Y., Wonanke A.D.D., Addicoat M.A., Pal S.K. A Dual-Function Highly Crystalline Covalent Organic Framework for HCl Sensing and Visible-Light Heterogeneous Photocatalysis. Macromolecules. 2021, 54(13): 6595-6604. DOI: https://doi.org/10.1021/acs.macromol.1c00574.

[19] Song C., Nie J., Ma C., Lu C., Wang F., Yang G. 1,2,3-Triazole-based conjugated porous polymers for visible light induced oxidative organic transformations. Appl. Catal. B: Environ. 2021, 287: 119984-119996. DOI: https://doi.org/10.1016/j.apcatb.2021.119984.

[20] Zhi Y., Ma S., Xia H., Zhang Y., Shi Z., Mu Y., Liu X. Construction of donor-acceptor type conjugated microporous polymers: A fascinating strategy for the development of efficient heterogeneous photocatalysts in organic synthesis. Appl. Catal. B: Environ. 2019, 244: 36-44. DOI: https://doi.org/10.1016/j.apcatb.2018.11.032.

[21] Zhang W., Li S., Tang X., Tang J., Pan C., Yu G. Phenothiazine core promoted charge transfer in conjugated microporous polymers for photocatalytic Ugi-type reaction and aerobic selenation of indoles. Appl. Catal. B: Environ. 2020, 272: 118982-118992. DOI: https://doi.org/10.1016/j.apcatb.2020.118982.

[22] Purser S., Moore P.R., Swallow S., Gouverneur V. Fluorine in Medicinal Chemistry. Chem. Soc. Rev. 2008, 37(2): 320-330. DOI: https://doi.org/10.1039/b610213c.

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Published

2024-01-01

Issue

Vol. 6 No. 2 (2024)

Section

Articles

DOI:

https://doi.org/10.61784/ejst3007

How to Cite

YongLi Tan, YeMu Zhu, HaiFeng Duan. T ruxenone and isotruxenone-based porous organic polymers as metal-free, heterogeneous photocatalysts for visible-light-promoted reduction of lung cancer A 549 cells. Eurasia Journal of Science and Technology. 2024, 6(2): 51-65. DOI: 10.61784/ejst3007 .