Rational design of fluorinated graphene-porphyrin nanoarchitectonics: integrating hydrophobicity to macromolecular heterocyclic systems
Source abstract
Abstract
Graphene-porphyrin hybrid materials with direct assembly between the fluorinated graphene (FG) nanosheets and the pre-formed 5,10,15,20-tetrakis(p-hydroxyphenyl)porphyrin (THPP) units have been successfully synthesized. The structure–property, binding, and assembly of THPP over FG nanosheets were methodically analyzed by spectroscopic, microscopic, and solvent wetting techniques. The solvent wetting characteristics and surface free energy of the supportless THPP and FG-supported THPP were investigated. The decoration of porphyrin over FG ensued in a surface free energy of 28.7 mJ m−2 directing to hydrophobic (WCA ~ 130 ± 2°) networks. Photo-physical studies demonstrated considerable non-covalent interactions between the THPP with FG multi-layers. The emission responses of THPP and FG-THPP with ferric complexes and its coordination with respect to the –philicity of the THPP were probed using photoluminescence spectroscopy. The functional groups blended in the FG-THPP inks were subjected to fuse with interconnected networks like cellulose paper and melamine sponge by exploiting the dispersion processability followed by morphology evaluation and water-wettability. Graphical abstract
Source: expertdata · Quality: candidate unverified · Source record ↗
Research context
OpenAlex topics: Porphyrin and Phthalocyanine Chemistry · Graphene research and applications · Surface Chemistry and Catalysis
SciVX discovery tags are terminology-based. OpenAlex topics are source-provided classifications.
References (59)
Show source-provided references
1. Ariga K (2021) Nanoarchitectonics with porphyrins and related molecules. J Porphyr Phthalocyanines 25(10n12):897–916. https://doi.org/10.1142/s108842462130005610.1142/s1088424621300056 ↗
2. Auwärter W, Écija D, Klappenberger F, Barth JV (2015) Porphyrins at interfaces Nat Chem 7(2):105–120. https://doi.org/10.1038/nchem.215910.1038/nchem.2159 ↗
3. Lu H, Kobayashi N (2016) Optically active porphyrin and phthalocyanine systems. Chem Rev 116(10):6184–6261. https://doi.org/10.1021/acs.chemrev.5b0058810.1021/acs.chemrev.5b00588 ↗
4. Senge MO, Sergeeva NN, Hale KJ (2021) Classic highlights in porphyrin and porphyrinoid total synthesis and biosynthesis. Chem Soc Rev 50(7):4730–4789. https://doi.org/10.1039/C7CS00719A10.1039/C7CS00719A ↗
5. Ishihara S, Labuta J, Van Rossom W, Ishikawa D, Minami K, Hill JP, Ariga K (2014) Porphyrin-based sensor nanoarchitectonics in diverse physical detection modes. Phys Chem Chem Phys 16(21):9713–9746. https://doi.org/10.1039/C3CP55431G10.1039/C3CP55431G ↗
6. Lim JM, Yoon ZS, Shin J-Y, Kim KS, Yoon M-C, Kim D (2008) The photophysical properties of expanded porphyrins: relationships between aromaticity, molecular geometry and non-linear optical properties. Chem Commun 3:273. https://doi.org/10.1039/B810718A10.1039/B810718A ↗
7. Bizaia N, de Faria EH, Ricci GP, Calefi PS, Nassar EJ, Castro KADF, Nakagaki S, Ciuffi KJ, Trujillano R, Vicente MA, Gil A, Korili SA (2009) Porphyrin−kaolinite as efficient catalyst for oxidation reactions. ACS Appl Mater Interfaces 1(11):2667–2678. https://doi.org/10.1021/am900556b10.1021/am900556b ↗
8. Canton-Vitoria R, Scharl T, Stergiou A, Cadranel A, Arenal R, Guldi DM, Tagmatarchis N (2020) Ping-pong energy transfer in covalently linked porphyrin-MoS2 architectures. Angew Chem Int Ed 59(10):3976–3981. https://doi.org/10.1002/anie.20191449410.1002/anie.201914494 ↗
9. Chen J, Zhu Y, Kaskel S (2021) Porphyrin-based metal–organic frameworks for biomedical applications. Angew Chem Int Ed 60(10):5010–5035. https://doi.org/10.1002/anie.20190988010.1002/anie.201909880 ↗
10. Chen R, Wang Y, Ma Y, Mal A, Gao X-Y, Gao L, Qiao L, Li X-B, Wu L-Z, Wang C (2021) Rational design of isostructural 2D porphyrin-based covalent organic frameworks for tunable photocatalytic hydrogen evolution. Nat Commun 12(1):1354. https://doi.org/10.1038/s41467-021-21527-310.1038/s41467-021-21527-3 ↗
11. Jin L, Lv S, Miao Y, Liu D, Song F (2021) Recent development of porous porphyrin-based nanomaterials for photocatalysis. ChemCatChem 13(1):140–152. https://doi.org/10.1002/cctc.20200117910.1002/cctc.202001179 ↗
12. Liang Z, Wang H-Y, Zheng H, Zhang W, Cao R (2021) Porphyrin-based frameworks for oxygen electrocatalysis and catalytic reduction of carbon dioxide. Chem Soc Rev 50(4):2540–2581. https://doi.org/10.1039/D0CS01482F10.1039/D0CS01482F ↗
13. Silvestri S, Fajardo AR, Iglesias BA (2022) Supported porphyrins for the photocatalytic degradation of organic contaminants in water: a review. Environ Chem Lett 20(1):731–771. https://doi.org/10.1007/s10311-021-01344-210.1007/s10311-021-01344-2 ↗
14. Wang C, Hao Y, Wang Y, Song H, Hussain S, Gao R, Gao L, He Y, Zheng G, Tang Y (2021) Multiwall carbon nanotubes non-covalently functionalized by porphyrin–Sn networks for protein adsorption. ACS Appl Nano Mater 4(3):2345–2350. https://doi.org/10.1021/acsanm.0c0321510.1021/acsanm.0c03215 ↗
15. Wei Y, Zhang M, Wu P, Luo J, Dai L, Li H, Wang L, She Y, Zhu W, Li H-m (2020) Tailoring electronic properties of porphyrin manganese on boron nitride for enhancing aerobic oxidative desulfurization at room temperature. ACS Sustain Chem Eng 8(2):1015–1022. https://doi.org/10.1021/acssuschemeng.9b0572810.1021/acssuschemeng.9b05728 ↗
16. Zhang N, Wang L, Wang H, Cao R, Wang J, Bai F, Fan H (2018) Self-assembled one-dimensional porphyrin nanostructures with enhanced photocatalytic hydrogen generation. Nano Lett 18(1):560–566. https://doi.org/10.1021/acs.nanolett.7b0470110.1021/acs.nanolett.7b04701 ↗
17. Fujimura T, Shimada T, Sasai R, Takagi S (2018) Optical humidity sensing using transparent hybrid film composed of cationic magnesium porphyrin and clay mineral. Langmuir 34(12):3572–3577. https://doi.org/10.1021/acs.langmuir.7b0400610.1021/acs.langmuir.7b04006 ↗
18. Monteiro AR, Neves MGPMS, Trindade T (2020) Functionalization of graphene oxide with porphyrins: synthetic routes and biological applications. ChemPlusChem 85(8):1857–1880. https://doi.org/10.1002/cplu.20200045510.1002/cplu.202000455 ↗
19. Zhang B, Gu Q, Wang C, Gao Q, Guo J, Wong PW, Liu CT, An AK (2021) Self-assembled hydrophobic/hydrophilic porphyrin-Ti3C2Tx MXene Janus membrane for dual-functional enabled photothermal desalination. ACS Appl Mater Interfaces 13(3):3762–3770. https://doi.org/10.1021/acsami.0c1605410.1021/acsami.0c16054 ↗
20. Bera R, Mandal S, Mondal B, Jana B, Nayak SK, Patra A (2016) Graphene–porphyrin nanorod composites for solar light harvesting. ACS Sustain Chem 4(3):1562–1568. https://doi.org/10.1021/acssuschemeng.5b0150410.1021/acssuschemeng.5b01504 ↗
21. Dasler D, Schäfer RA, Minameyer MB, Hitzenberger JF, Hauke F, Drewello T, Hirsch A (2017) Direct covalent coupling of porphyrins to graphene. J Am Chem Soc 139(34):11760–11765. https://doi.org/10.1021/jacs.7b0412210.1021/jacs.7b04122 ↗
22. Du Y, Dong N, Zhang M, Zhu K, Na R, Zhang S, Sun N, Wang G, Wang J (2017) Covalent functionalization of graphene oxide with porphyrin and porphyrin incorporated polymers for optical limiting. Phys Chem Chem Phys 19(3):2252–2260. https://doi.org/10.1039/C6CP05920A10.1039/C6CP05920A ↗
23. Gacka E, Burdzinski G, Marciniak B, Kubas A, Lewandowska-Andralojc A (2020) Interaction of light with a non-covalent zinc porphyrin–graphene oxide nanohybrid. Phys Chem Chem Phys 22(24):13456–13466. https://doi.org/10.1039/D0CP02545C10.1039/D0CP02545C ↗
24. Gacka E, Wojcik A, Mazurkiewicz-Pawlicka M, Malolepszy A, Stobiński L, Kubas A, Hug GL, Marciniak B, Lewandowska-Andralojc A (2019) Noncovalent porphyrin–graphene oxide nanohybrids: the pH-dependent behavior. J Phys Chem C 123(6):3368–3380. https://doi.org/10.1021/acs.jpcc.8b1137410.1021/acs.jpcc.8b11374 ↗
25. Karousis N, Sandanayaka ASD, Hasobe T, Economopoulos SP, Sarantopoulou E, Tagmatarchis N (2011) Graphene oxide with covalently linked porphyrin antennae: synthesis, characterization and photophysical properties. J Mater Chem 21(1):109–117. https://doi.org/10.1039/C0JM00991A10.1039/C0JM00991A ↗
26. Mondal B, Bera R, Nayak SK, Patra A (2016) Graphene induced porphyrin nano-aggregates for efficient electron transfer and photocurrent generation. J Mater Chem C 4(25):6027–6036. https://doi.org/10.1039/C6TC01580H10.1039/C6TC01580H ↗
27. Wang A, Song J, Jia D, Yu W, Long L, Song Y, Cifuentes MP, Humphrey MG, Zhang L, Shao J, Zhang C (2016) Functionalization of reduced graphene oxide with axially-coordinated metal-porphyrins: facile syntheses and temporally-dependent nonlinear optical properties. Inorg Chem Front 3(2):296–305. https://doi.org/10.1039/C5QI00209E10.1039/C5QI00209E ↗
28. Xu Y, Liu Z, Zhang X, Wang Y, Tian J, Huang Y, Ma Y, Zhang X, Chen Y (2009) A graphene hybrid material covalently functionalized with porphyrin: synthesis and optical limiting property. Adv Mater 21(12):1275–1279. https://doi.org/10.1002/adma.20080161710.1002/adma.200801617 ↗
29. Yamuna R, Ramakrishnan S, Dhara K, Devi R, Kothurkar NK, Kirubha E, Palanisamy PK (2013) Synthesis, characterization, and nonlinear optical properties of graphene oxide functionalized with tetra-amino porphyrin. J Nanoparticle Res 15(1):1399. https://doi.org/10.1007/s11051-012-1399-y10.1007/s11051-012-1399-y ↗
30. Datta KKR, Zboril R (2014) Halogenated graphenes: emerging family of two-dimensional materials. Wiley-VCH Verlag GmbH & Co. KGaA, Functionalization of Graphene. https://doi.org/10.1002/9783527672790.ch610.1002/9783527672790.ch6 ↗
31. Karlický F, Kumara Ramanatha Datta K, Otyepka M, Zbořil R (2013) Halogenated graphenes: rapidly growing family of graphene derivatives. ACS Nano 7(8):6434–6464. https://doi.org/10.1021/nn402402710.1021/nn4024027 ↗
32. Chen X, Fan K, Liu Y, Li Y, Liu X, Feng W, Wang X (2022) Recent advances in fluorinated graphene from synthesis to applications: critical review on functional chemistry and structure engineering. Adv Mater 34(1):2101665. https://doi.org/10.1002/adma.20210166510.1002/adma.202101665 ↗
33. Matochová D, Medved M, Bakandritsos A, Steklý T, Zbořil R, Otyepka M (2018) 2D Chemistry: chemical control of graphene derivatization. J Phys Chem Lett 9(13):3580–3585. https://doi.org/10.1021/acs.jpclett.8b0159610.1021/acs.jpclett.8b01596 ↗
34. Borse RA, Kale MB, Sonawane SH, Wang Y (2022) Fluorographene and its composites: fundamentals, electrophysical properties, DFT studies, and advanced applications. Adv Funct Mater 32(26):2202570. https://doi.org/10.1002/adfm.20220257010.1002/adfm.202202570 ↗
35. Luo Z, Wang X, Chen D, Chang Q, Xie S, Ma Z, Lei W, Pan J, Pan Y, Huang J (2021) Ultrafast Li/fluorinated graphene primary batteries with high energy density and power density. ACS Appl Mater Interfaces 13(16):18809–18820. https://doi.org/10.1021/acsami.1c0206410.1021/acsami.1c02064 ↗
36. Prasanthi I, Raidongia K, Datta KKR (2021) Super-wetting properties of functionalized fluorinated graphene and its application in oil–water and emulsion separation. Mater Chem Front 5(16):6244–6255. https://doi.org/10.1039/d1qm00757b10.1039/d1qm00757b ↗
37. Ravi Y, Prasanthi I, Behera S, Datta KKR (2022) MIL-101(Fe) networks supported on fluorinated graphene nanosheets as coatings for oil sorption. ACS Appl Nano Mater 5(4):5857–5867. https://doi.org/10.1021/acsanm.2c0108310.1021/acsanm.2c01083 ↗
38. Šedajová V, Bakandritsos A, Błoński P, Medveď M, Langer R, Zaoralová D, Ugolotti J, Dzíbelová J, Jakubec P, Kupka V, Otyepka M (2022) Nitrogen doped graphene with diamond-like bonds achieves unprecedented energy density at high power in a symmetric sustainable supercapacitor. Energy Environ Sci 15(2):740–748. https://doi.org/10.1039/D1EE02234B10.1039/D1EE02234B ↗
39. Ye X, Ma L, Yang Z, Wang J, Wang H, Yang S (2016) Covalent functionalization of fluorinated graphene and subsequent application as water-based lubricant additive. ACS Appl Mater Interfaces 8(11):7483–7488. https://doi.org/10.1021/acsami.5b1057910.1021/acsami.5b10579 ↗
40. Yogapriya R, Datta KKR (2020) Porous fluorinated graphene and ZIF-67 composites with hydrophobic-oleophilic properties towards oil and organic solvent sorption. J Nanosci Nanotechnol 20(5):2930–2938. https://doi.org/10.1166/jnn.2020.1746510.1166/jnn.2020.17465 ↗
41. Yogapriya R, Kasibhatta KRD (2020) Hydrophobic-superoleophilic fluorinated graphene nanosheet composites with metal–organic framework HKUST-1 for oil–water separation. ACS Appl Nano Mater 3(6):5816–5825. https://doi.org/10.1021/acsanm.0c0098010.1021/acsanm.0c00980 ↗
42. Zoppellaro G, Bakandritsos A, Tuček J, Błoński P, Susi T, Lazar P, Bad’ura Z, Steklý T, Opletalová A, Otyepka M, Zbořil R (2019) Microwave energy drives “On–Off–On” spin-switch behavior in nitrogen-doped graphene. Adv Mater 31(37):1902587. https://doi.org/10.1002/adma.20190258710.1002/adma.201902587 ↗
43. Jeon K-J, Lee Z, Pollak E, Moreschini L, Bostwick A, Park C-M, Mendelsberg R, Radmilovic V, Kostecki R, Richardson TJ, Rotenberg E (2011) Fluorographene: a wide bandgap semiconductor with ultraviolet luminescence. ACS Nano 5(2):1042–1046. https://doi.org/10.1021/nn102527410.1021/nn1025274 ↗
44. Okotrub AV, Chekhova GN, Pinakov DV, Yushina IV, Bulusheva LG (2022) Optical absorption and photoluminescence of partially fluorinated graphite crystallites. Carbon 193:98–106. https://doi.org/10.1016/j.carbon.2022.03.03410.1016/j.carbon.2022.03.034 ↗
45. Papadakis I, Kyrginas D, Stathis A, Couris S, Potsi G, Bourlinos AB, Tomanec O, Otyepka M, Zboril R (2019) Large enhancement of the nonlinear optical response of fluorographene by chemical functionalization: the case of diethyl-amino-fluorographene. J Phys Chem C 123(42):25856–25862. https://doi.org/10.1021/acs.jpcc.9b0749310.1021/acs.jpcc.9b07493 ↗
46. Stathis A, Papadakis I, Karampitsos N, Couris S, Potsi G, Bourlinos AB, Otyepka M, Zboril R (2019) Thiophenol-modified fluorographene derivatives for nonlinear optical applications. ChemPlusChem 84(9):1288–1298. https://doi.org/10.1002/cplu.20180064310.1002/cplu.201800643 ↗
47. Stathis A, Stavrou M, Papadakis I, Bakandritsos A, Steklý T, Otyepka M, Couris S (2020) Octylamine-modified fluorographenes as a versatile platform for the efficient engineering of the nonlinear optical properties of fluorinated graphenes. Adv photonics 1(2):2000014. https://doi.org/10.1002/adpr.20200001410.1002/adpr.202000014 ↗
48. Ariga K (2021) Nanoarchitectonics revolution and evolution: from small science to big technology. Small Science 1(1):2000032. https://doi.org/10.1002/smsc.20200003210.1002/smsc.202000032 ↗
49. Ariga K (2021) Nanoarchitectonics: what’s coming next after nanotechnology? Nanoscale Horiz 6(5):364–378. https://doi.org/10.1039/D0NH00680G10.1039/D0NH00680G ↗
50. Chaikittisilp W, Yamauchi Y, Ariga K (2022) Material evolution with nanotechnology, nanoarchitectonics, and materials informatics: what will be the next paradigm shift in nanoporous materials? Adv Mater 34(7):2107212. https://doi.org/10.1002/adma.20210721210.1002/adma.202107212 ↗
51. Chen Y, Huang Z-H, Yue M, Kang F (2014) Integrating porphyrin nanoparticles into a 2D graphene matrix for free-standing nanohybrid films with enhanced visible-light photocatalytic activity. Nanoscale 6(2):978–985. https://doi.org/10.1039/C3NR04908F10.1039/C3NR04908F ↗
52. Jing J, Yang J, Li W, Wu Z, Zhu Y (2022) Construction of interfacial electric field via dual-porphyrin heterostructure boosting photocatalytic hydrogen evolution. Adv Mater 34(3):2106807. https://doi.org/10.1002/adma.20210680710.1002/adma.202106807 ↗
53. Gkini K, Verykios A, Balis N, Kaltzoglou A, Papadakis M, Adamis KS, Armadorou K-K, Soultati A, Drivas C, Gardelis S, Petsalakis ID, Palilis LC, Fakharuddin A, Haider MI, Bao X, Kennou S, Argitis P, Schmidt-Mende L, Coutsolelos AG, Falaras P, Vasilopoulou M (2020) Enhanced organic and perovskite solar cell performance through modification of the electron-selective contact with a bodipy–porphyrin dyad. ACS Appl Mater Interfaces 12(1):1120–1131. https://doi.org/10.1021/acsami.9b1758010.1021/acsami.9b17580 ↗
54. Min KS, Manivannan R, Son Y-A (2019) Porphyrin Dye/TiO2 imbedded PET to improve visible-light photocatalytic activity and organosilicon attachment to enrich hydrophobicity to attain an efficient self-cleaning material. Dyes Pigm 162:8–17. https://doi.org/10.1016/j.dyepig.2018.10.01410.1016/j.dyepig.2018.10.014 ↗
55. Reddy G, Katakam R, Devulapally K, Jones LA, Della Gaspera E, Upadhyaya HM, Islavath N, Giribabu L (2019) Ambient stable, hydrophobic, electrically conductive porphyrin hole-extracting materials for printable perovskite solar cells. J Mater Chem C 7(16):4702–4708. https://doi.org/10.1039/C9TC00605B10.1039/C9TC00605B ↗
56. Kitazaki Y, Hata T (1972) Surface-chemical criteria for optimum adhesion. J Adhes 4(2):123–132. https://doi.org/10.1080/0021846720807221710.1080/00218467208072217 ↗
57. Law K-Y, Zhao H (2016) Determination of solid surface tension by contact angle. In: Law K-Y, Zhao H (eds) Surface wetting: characterization, contact angle, and fundamentals. Springer International Publishing, Cham, pp 135–148. https://doi.org/10.1007/978-3-319-25214-8_710.1007/978-3-319-25214-8_7 ↗
58. Larowska D, Wojcik A, Mazurkiewicz-Pawlicka M, Malolepszy A, Stobiński L, Marciniak B, Lewandowska-Andralojc A (2019) Cationic porphyrin-graphene oxide hybrid: donor-acceptor composite for efficient photoinduced electron transfer. ChemPhysChem 20(8):1054–1066. https://doi.org/10.1002/cphc.20190004010.1002/cphc.201900040 ↗
59. Qi Z-L, Cheng Y-H, Xu Z, Chen M-L (2020) Recent advances in porphyrin-based materials for metal ions detection. Int J Mol Sci 21(16):5839. https://doi.org/10.3390/ijms2116583910.3390/ijms21165839 ↗