Department of Chemistry and Chemical Engineering, and Beijing Key Laboratory for Green Catalysis and Separation, Beijing University of Technology, Beijing 100124
Abstract: Porphyrin is a special kind of conjugate aromatic macrocyclic compounds. It can form different types of aggregates under different conditions through non-covalent bond interaction. The aggregate behaviors of porphyrin compounds are reviewed. Different aggregates formed by different porphyrins under different conditions are introduced in detail. The aggregation structure and the corresponding effect factors are emphatically discussed. In addition, the prospect of porphyrin aggregation is forecasted.
1 Ryan A, Gehrold A, Perusitti R, et al. Porphyrin dimers and arrays[J]. Eur J Organ Chem,2011,2011(29):5817. 2 Verma S, Ghosh H N. Exciton energy and charge transfer in porphyrin aggregate/semiconductor (TiO2) composites[J]. J Phys Chem Lett,2012,3(14):1877. 3 Singh S, Aggarwal A, Arianna G, et al. Glycosylated porphyrins, phthalocyanines, and other porphyrinoids for diagnostics and therapeutics[J]. Chem Rev,2015,115(18):10261. 4 Lucky S S, Soo K C, Zhang Y. Nanoparticles in photodynamic therapy[J]. Chem Rev,2015,115(4):1990. 5 Snitka V, Rackaitis M, Rodaite R. Assemblies of TPPS4 porphyrin investigated by TEM, SPM and UV-vis spectroscopy[J]. Sensors Actuators B: Chem,2005,109(1):159. 6 Gandini S C, Gelamo E L, Iltri R, et al. Small angle X-ray scattering study of meso-tetrakis (4-sulfonatophenyl) porphyrin in aqueous solution: A self-aggregation model[J]. Biophys J, 2003, 85(2):259. 7 Zhou M, Ouyang S L, Liu Z, et al. Orientation change of porphyrin in aggregate caused by counterion[J]. Vibrational Spectroscopy,2009,49(1):7. 8 Okada S, Segawa H. Substituent-control exciton in J-aggregates of protonated water-insoluble porphyrins[J]. J Am Chem Soc,2003,125(9):2792. 9 Yildirim H, Iseri E I, Gulen D. A quantitative analysis of excitonicsuperhyperchromism in porphyrin J-/H-aggregates[J]. Chem Phys Lett,2004,391(4-6):302. 10 Ma C, Zhang Y H, Fu C S, et al. Different aggregation behaviors of tetra-(4-hydroxyphenyl) porphyrin (THPPH2) in the inner core and on the surface of CTAB micelles[J]. Chin Chem Lett,2000,11(10):929. 11 Ghosh A, Selvamani T, Jose D A, et al. Generation of nanostructures by the aggregation of porphyrin derivatives with long alkane chain in mix-solvent[J]. J Nanomater,2007,2007(1):2. 12 Maiti N C, Mazumdar S, Periasamy N. J- and H-aggregates of porphyrin-surfactant complexes: Time-resolved fluorescence and other spectroscopic studies[J]. J Phys Chem B,1998,102(9):1528. 13 Li X W, Li D J, Han M Y, et al. Neutral porphyrin J-aggregates in premicellar SDS solution[J]. Colloids Surf A: Physicochem Eng Aspects,2005,256(2-3):151. 14 Pasternack R F, Fleming C, Herring S, et al. Aggregation kinetics of extended porphyrin and cyanine dye assemblies[J]. Biophys J,2000,79(1):550. 15 Kubat P, Lang K, Prochakova K, et al. Self-aggregates of cationic meso-tetratolylporphyrins in aqueous solutions[J]. Langmuir,2003,19(2):422. 16 Choi M Y, Pollard J A, Webb M A, et al. Counterion-dependent excitonic spectra of tetra(p-carboxyphenyl) porphyrin aggregates in acidic aqueous solution[J]. J Am Chem Soc,2003,125(3):810. 17 Liao Bo, Ye Wenbo. The aggregation behaviors of meso-tetrakis(4-sulphonatophenyl) porphine in chitin film[J]. J Hunan University of Science & Technology:Nat Sci Ed,2009,24(4):113(in Chinese). 廖博, 叶文波. 四 (4-磺酸基苯基)卟啉在甲壳素膜上的聚集行为研究[J]. 湖南科技大学学报:自然科学版,2009,24(4):113. 18 Li M, Zhao L Z, Zhang Y C, et al. Adsorption behavior and self-aggregation of 5,10,15,20-tetrakis-(4-sulfonatophenyl)-porphyrin on quaternized polysulfone membrane[J]. Colloid Polym Sci,2015,293(2):513. 19 Gradova M A, Lobanov A V. Photophysical properties and aggregation behavior of transition metal tetraphenylporphyrin tetrasulfonate complexes in microheterogeneous media[J]. Macroheterocycles,2013,6(4):340. 20 Zhao L Z, Ma R J, Li J B, et al. J- and H-aggregates of 5,10,15,20-tetrakis-(4-sulfonatophenyl)-porphyrin and interconversion in PEG-b-P4VP micelles[J]. Biomacromolecules,2008,9(10):2601. 21 Egawa Y, Hayashida R, Anzai J I. pH-induced interconversion between J-aggregates and H-aggregates of 5,10,15,20-tetrakis(4-sulfonatophenyl) porphyrin in polyelectrolyte multilayer films[J]. Langmuir,2007,23(26):13146. 22 Ma Huili. Studies on the interaction between meso-terakis(p-sulfo-natophenyl) porphyrin J-aggregates and ct-DNA[J]. Chem Res Application,2012,24(11):1642 (in Chinese). 马惠莉. J-聚集态下中位-四(对-磺酸基苯基)卟啉与ct-DNA相互作用的研究[J]. 化学研究与应用,2012,24(11):1642. 23 Aggarwal L P F, Borissevitch I E. On the dynamics of the TPPS4 aggregation in aqueous solutions-successive formation of H and J aggregates[J]. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy,2006,63(1):227. 24 Ali M, Pandey S. Aggregation behavior of aqueous tetrakis(4-sulfonatophenyl) porphyrin in the presence of 1-butyl-3-methylimidazolium tetrafluoroborate[J]. J Photochem Photobiology A: Chem,2009,207(2-3):288. 25 Rubires R, Crusats J, EI-Hachemi Z, et al. Self-assembly in water of the sodium salts of meso-sulfonatophenyl substituted porphyrins[J]. New J Chem,1999,23(2):189. 26 Poderys V, Selskis A, Rotomskis R. The polar sulfonic groups influence on structure of self-assembled tetrapyrrolic molecules[J]. Solid State Phenomena, 2004, 97-98:221. 27 Matsumoto J, Tanimura S, Shiragami T, et al. Concentration-dependent aggregation of water-soluble phosphorus porphyrin in an aqueous solution[J]. J Porphyr Phthalocyan,2012, 16(2):210. 28 Uemori Y, Munakata H, Kitazawa S, et al. Optically active J-aggregate formed from water-soluble porphyrin with phenylalanine[J]. J Porphyr Phthalocyan,2012,16(12):1285. 29 Cho Y, Lee J H, Jaworski J, et al. The influence of ultrasound on porphyrin-based metallogel formation: Efficient control of H- and J-type aggregations[J]. New J Chem,2012,36(1):32. 30 Serra V V, Andrade S M, Neves M, et al. J-aggregate formation in bis-(4-carboxyphenyl) porphyrins in water:pH and counterion dependence[J]. New J Chem,2010,34(12):2757. 31 Sehlstedt U, Kim S K, Carter P, et al. Interaction of cationic porphyrins with DNA[J]. Biochemistry,1994,33(2):417. 32 Granville D J, McManus B M, Hunt D W C. Photodynamic therapy: Shedding light on the biochemical pathways regulating porphyrin-mediated cell death[J]. Histology Histopathology,2001,16(1):309. 33 Hou Anxin, Liu Yi, Huang Weiguo, et al. Interaction of Y3+ and its cationic monoporphyrinate complex with staphylococcus aureus[J]. Acta Chim Sin,2003,61(9): 1382 (in Chinese). 侯安新,刘义,黄伟国,等. 钇离子及其阳离子卟啉配合物与金黄色葡萄球菌的相互作用[J].化学学报,2003,61(9):1382. 34 Onuki J, Ribas A V, Medeiros M H G, et al. Supramolecularcationic tetraruthenated porphyrin induces single-strand breaks and 8-oxo-7,8-dihydro-2′-deoxyguanosineformationin DNA in the presence of light[J]. Photochem Photobiol,1996,63(3):272. 35 Kano K, Minamizono H, Kitae T, et al. Self-aggregation of cationic porphyrins in water. Can π-π stacking interaction overcome electrostatic repulsive force[J]. J Phys Chem A,1997,101(34):6118. 36 Kano K, Fukuda K, Wakami H, et al. Factors influencing self-aggregation tendencies of cationic porphyrins in aqueous solution[J]. J Am Chem Soc,2000,122(31):7494. 37 Castriciano M A, Samperi M, Camiolo S, et al. Unusual stepwise protonation and J-aggregation of meso-tetrakis(N-methylpyridinium-4-yl) porphine on binding poly(sodium vinylsulfonate)[J]. Chem — A Eur J,2013,19(36):12161. 38 Ma Hongmin, Chen Xin, Sun Shuting, et al. Study on the aggregation behavior of cationic porphyrins and their interaction with ctDNA[J]. Spectroscopy Spectral Anal,2009,29(2): 423(in Chinese). 马洪敏,陈欣,孙舒婷,等. 水溶性阳离子卟啉与ctDNA的相互作用及其聚集行为研究[J]. 光谱学与光谱分析,2009,29(2):423. 39 Ding K W, Wang F, Wu Feipeng. Association behavior of porphyrin pendants in pH-sensitive water-soluble polymer[J]. Chinese J Polym Sci,2012,30(1):63. 40 Zozulya V N, Ryazanova O A, Voloshin I M, et al. Self-assemblies of tricationic porphyrin on inorganic polyphosphate[J]. Biophys Chem,2014,185:39. 41 Liu Bowen, Guo Dongsheng, Song Baoe, et al. Aggregation behaviors of novel dicationic porphyrin and ultrasound-induced aggregation transformation[J]. Sci Sin Chim,2011,41(4):741(in Chinese). 刘博闻,郭东升,宋保娥,等. 新型双阳离子卟啉的聚集行为及超声诱导的转换[J]. 中国科学:化学,2011,41(4):741. 42 de Miguel G, Hosomizu K, Umeyama T, et al. J-aggregation of a sulfonated amphiphilic porphyrin at the air-water interface as a function of pH[J]. J Colloid Interface Sci,2011,356(2):775. 43 Hosomizu K, Oodoi M, Umeyama T, et al. Substituent effects of porphyrins on structures and photophysical properties of amphiphilic porphyrin aggregates[J]. J Phys Chem B,2008,112(51):16517. 44 Guo L.Side-chain-controlled H- and J-aggregation of amphiphilic porphyrins in CTAB micelles[J].J Colloid Interface Sci,2008,322(1):281. 45 Morisue M, Morita T, Kuroda Y. Ligand-assisted J-type aggregates of zinc porphyrin: Anticooperative molecular organization in self-assembled bolaamphiphile[J]. Organ Biomolecular Chem,2010,8(15):3457. 46 Kano K. Porphyrin-cyclodextrin supramolecular complexes as myoglobin model in water[J]. Colloid Polym Sci,2008,286(1):79. 47 Liu Yun, Pan Jinghao. Progress in cyclodextrin-porphyrin supramolecular system[J]. Chinese J Analyt Chem,2005,33(1):129(in Chinese). 刘芸,潘景浩. 环糊精-卟啉超分子体系研究进展[J]. 分析化学,2005,33(1):129. 48 Sortino S,et al.Nanoparticles of cationic amphiphilic cyclodextrins entangling anionic porphyrins as carrier-sensitizer system in photodynamic cancer therapy[J].Biomaterials,2006,27(23):4256. 49 Mazzaglia A, Bondi M L, Scala A, et al. Supramolecular assemblies based on complexes of nonionic amphiphilic cyclodextrins and a meso-tetra(4-sulfonatophenyl) porphine tributyltin(Ⅳ) derivative: Potential nanotherapeutics against melanoma[J]. Biomacromolecules,2013,14(11):3820. 50 Ma H L, Wu J J, Liang W J, et al. Study on the association phenomenon of cyclodextrin to porphyrin J-aggregates by NMR spectroscopy[J]. J Inclusion Phenomena Macrocyclic Chem,2007,58(3-4):221. 51 EL-Hachemi Z, Farrera J A, García-Ortega H, et al. Heteroassociation of meso-sulfonatophenylporphyrins with β- and γ-cyclodextrin [J]. J Porphyr Phthalocyan,2001,5(5):465. 52 Kano K, Nishiyabu R, Doi R. Novel behavior of O-methylated β-cyclodextrins in inclusion of meso-tetraarylporphyrins[J]. J Organ Chem,2005,70(9):3667. 53 Ribo J M, Farrera J A, Valero M L, et al. Self-assembly of cyclodextrins with meso-tetrakis(4-sulfonatophenyl) porphyrin in aqueous solution[J]. Tetrahedron,1995,51(12): 3705. 54 Wu J J, Ma H L, Mao H S, et al. Investigation on disassociation of porphyrin J-aggregates induced by β-cyclodextrins using absorption and fluorescence spectroscopy[J]. J Photochem Photobiol A—Chem,2005,173(3):296. 55 Wang X P, Pan J H, Shuang S M, et al. Study on the supramolecular system of TAPP and cyclodextrins by spectroscopy[J]. Supramolecular Chem,2003,15(4):245. 56 Toncelli C, Pino-Pinto J P, Sano N, et al. Controlling the aggregation of 5,10,15,20-tetrakis-(4-sulfonatophenyl)-porphyrin by the use of polycations derived from polyketones bearing charged aromatic groups[J]. Dyes Pigments,2013,98(1):51. 57 Wen Xin, Wang Sujuan, Gao Baoxiang, et al. Study of the aggregation of meso-tetrakis(4-hydroxyphenyl) porphyrin in the hyperbranched poly(amide-ester)solution[J]. Acta Chim Sin,2010,68(18):1876 (in Chinese). 温昕,王素娟,高保祥,等. 超支化聚(酰胺-酯)溶液中的 5,10,15,20-四 (4-羟基苯基)卟啉聚集行为的研究[J]. 化学学报,2010,68(18):1876. 58 Occhiuto I, De Luca G, Trapani M, et al. Peripheral stepwise degradation of a porphyrin J-aggregate[J]. Inorgan Chem,2012,51(19):10074.
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2017, Vol. 31 
