Review on N-confused porphyrin
DOI:
https://doi.org/10.52756/ijerr.2022.v29.006Keywords:
Porphyrin, confusion, N-confused, pyrrole, doubly N-confused, supramolecularAbstract
We all know how vital porphyrin is to our body, from binding haemoglobin and iron to carrying oxygen to our organs and tissues. Recently, there has been a discovery about a new isomer of porphyrin called N-confused porphyrin. Its chemistry is very different and exciting. From there, scientists have explored many corners of this confusion chemistry, from doubly confused coordination to its supramolecular architecture, it has an identical backbone structure as porphyrin (1,1,1,1). NCP, on the other hand, has an additional pyrrolic moiety called a "confused pyrrole" that is linked to the surrounding meso-carbons at the ? and ?-positions. The position of pyrrolic N-H and ?-CH are shifted as a result of this unusual linkage. Resulting, NCP contains an NNNC core and an outward-pointing N atom. When a metal is co-ordinated in the core, a kind of organometallic complex having a carbon-metal bond is formed. On the other hand, the peripheral nitrogen atom serves as a H-bonding donor/acceptor and a metal coordination site.
References
Araki, K., Engelmann, F. M., Mayer, I., Toma, H. E., Baptista, M. S., Maeda, H., Osuka, A., & Furuta, H. (2003). Doubly N-confused porphyrins as efficient sensitizers for singlet oxygen generation. Chemistry Letters, 32(3), 244–245. 10.1246/cl.2003.244
Biscaglia, F., & Gobbo, M. (2018). Porphyrin–peptide conjugates in biomedical applications. Peptide Science, 110(5), e24038. 10.1002/pep2.24038
Bohle, D. S., Chen, W. C., & Hung, C. H. (2002). Metal oxidation promoted C-H activation in manganese complexes of N-confused porphyrin. Inorganic Chemistry, 41(13), 3334–3336. 10.1021/ic025573m
Chen, W. C., & Hung, C. H. (2001). Synthesis and characterization of iron N-confused porphyrins: Structural evidences of agostic interaction. Inorganic Chemistry, 40(20), 5070–5071. doi: 10.1021/ic0155333
Chmielewski, P. J., & Latos-Grazyński, L. (2000). Reactions of nickel(II) 2,21-dimethyl-2-aza-21-carbaporphyrin with phenyl grignard reagents, phenyllithium, and n-butyllithium. In Inorganic Chemistry, 39(25), 5639–5647). doi: 10.1021/ic000052p
Chmielewski, P.J. (2004). Synthesis and Characterization of a Directly Linked N-Confused Porphyrin Dimer. Angewandte Chemie, 116(42), 5773–5776. doi: 10.1002/ange.200461361
Chmielewski, P. J. (2005). Synthesis and Characterization of a Cyclic Bis-silver(I) Assembly of Four 2-Aza-21-carbaporphyrinatosilver(III) Subunits. Angewandte Chemie, 117(39), 6575–6578. doi: 10.1002/ange.200502208
Chmielewski, P. J., Latos‐Grażyński, L., Rachlewicz, K., & Glowiak, T. (1994). Tetra‐p‐tolylporphyrin with an Inverted Pyrrole Ring: A Novel Isomer of Porphyrin. Angewandte Chemie International Edition in English, 33(7), 779–781. 10.1002/anie.199407791
Engelmann, F. M., Mayer, I., Araki, K., Toma, H. E., Baptista, M. S., Maeda, H., Osuka, A., & Furuta, H. (2004). Photochemistry of doubly N-confused porphyrin bonded to non-conventional high oxidation state Ag(III) and Cu(III) ions. Journal of Photochemistry and Photobiology A: Chemistry, 163(3), 403–411. doi: 10.1016/j.jphotochem.2004.01.010
Fan, J., Whiteford, J. A., Olenyuk, B., Levin, M. D., Stang, P. J., & Fleischer, E. B. (1999). Self-assembly of porphyrin arrays via coordination to transition metal bisphosphine complexes and the unique spectral properties of the product metallacyclic ensembles. Journal of the American Chemical Society, 121(12), 2741–2752. doi: 10.1021/ja9839825
Furuta, H., Ishizuka, T., Osuka, A., Dejima, H., Nakagawa, H., & Ishikawa, Y. (2001). NH tautomerism of N-confused porphyrin [2]. Journal of the American Chemical Society, 123(25), 6207–6208. doi: 10.1021/ja010237a
Furuta, H., Kubo, N., Maeda, H., Ishizuka, T., Osuka, A., Nanami, H., & Ogawa, T. (2000). N-confused double-decker porphyrins. Inorganic Chemistry, 39(24), 5424–5425. doi: 10.1021/ic0010048
Furuta, H., Ishizuka, T., & Osuka, A. (2002). Flexible inner and outer coordination of Zn(II) N-confused porphyrin complex. Journal of the American Chemical Society, 124(20), 5622–5623. doi: 10.1021/ja017016p
Furuta, H., Ishizuka, T., Osuka, A., & Ogawa, T. (2000). “N-fused porphyrin”: A new tetrapyrrolic porphyrinoid with a fused tri- pentacyclic ring. Journal of the American Chemical Society, 122(24), 5748–5757. doi: 10.1021/ja000148i
Furuta, H., Ishizuka, T., Osuka, A., Uwatoko, Y., & Ishikawa, Y. (2001). Metal complexes of an N-confused calix[4]phyrin derivative - The first X-ray structure of an organometallic compound of divalent copper. Angewandte Chemie - International Edition, 40(12), 2323–2325. 10.1002/1521-3773(20010618)40:12<2323::AID-ANIE2323>3.0.CO;2-F
Furuta, H., Maeda, H., & Osuka, A. (2001a). Oxyindolophyrin: A Novel Fluoride Receptor Derived from N-Confused Corrole Isomer. Journal of the American Chemical Society, 123(26), 6435–6436. doi: 10.1021/ja015892x
Furuta, H., Maeda, H., & Osuka, A. (2001b). Theoretical Study of Stability, Structures, and Aromaticity of Multiply N-Confused Porphyrins. The Journal of Organic Chemistry, 66(25), 8563–8572. doi: 10.1021/jo016051b
Furuta, H., Maeda, H., & Osuka, A. (2002). Confusion, inversion, and creation - A new spring from porphyrin chemistry. Chemical Communications, 17, 1795–1804. doi: 10.1039/b200525p
Furuta, H., Maeda, H., Osuka, A., Yasutake, M., Shinmyozu, T., & Ishikawa, Y. (2000). Inner c-arylation of a doubly n-confused porphyrin-pd complex in toluenethe possibility of a pd3+ intermediate. Chemical Communications, 13, 1143–1144. doi: 10.1039/b003022h
Furuta, H., Morimoto, T., & Osuka, A. (2003). Syntheses, Structures, and Crystal Packing of N-Confused 5, 20-Diphenylporphyrin and Ag ( III ). American Chemical Society, 5(9), 2–5.
Furuta, H., Morimoto, T., & Osuka, A. (2004). Structures and Ligand Exchange of N-Confused Porphyrin Dimer Complexes with Group 12 Metals. Inorganic Chemistry, 43(5), 1618–1624. doi: 10.1021/ic035294e
Furuta, H., Ogawa, T., Uwatoko, Y., & Araki, K. (1999). N-Confused Tetraphenylporphyrin−Silver(III) Complex 1. Inorganic Chemistry, 38(11), 2676–2682. doi: 10.1021/ic9901416
Harvey, J. D., & Ziegler, C. J. (2003). Manganese N-confused porphyrin reactivity: CH bond activation and meso carbon reductionElectronic supplementary information (ESI) available: absorption spectra for 3 and 4. See http://www.rsc.org/suppdata/cc/b3/b310522a/. Chemical Communications, 162(23), 2890. doi: 10.1039/b310522a
Harvey, J. D., Ziegler, C. J., Telser, J., Ozarowski, A., & Krzystek, J. (2005). High-frequency and -field EPR investigation of a manganese(III) N-confused porphyrin complex, [Mn(NCTPP)(py)2]. Inorganic Chemistry, 44(13), 4451–4453. 10.1021/ic0506759
Hiroyuki F., Katsuyuki Y., Hiromitsu M., & Osuka, A. (2003). Pt Complexes of N-Confused Porphyrin: Facile Formation of N-Confused Porphyrin Dimers by Platinum(ii) Coordination to the Outer- Nitrogen Atoms. Angewandte Chemie, 115(19), 2236–2238. https://doi.org/10.1002/ange.200350995
Hung, C. H., Chen, W. C., Lee, G. H., & Peng, S. M. (2002). Dimeric iron n-confused porphyrin complexes. Chemical Communications, 2(14), 1516–1517. doi: 10.1039/b202679a
Ikawa, Y., Ogawa, H., Harada, H., & Furuta, H. (2008). N-confused porphyrin possessing glucamine-appendants: Aggregation and acid/base properties in aqueous media. Bioorganic and Medicinal Chemistry Letters, 18(24), 6394–6397. doi: 10.1016/j.bmcl.2008.10.079
Ishihara, S., Labuta, J., Van Rossom, W., Ishikawa, D., Minami, K., Hill, J. P., & Ariga, K. (2014). Porphyrin-based sensor nanoarchitectonics in diverse physical detection modes. Physical Chemistry Chemical Physics, 16(21), 9713–9746. doi: 10.1039/c3cp55431g
Ishizuka, T., Osuka, A., & Furuta, H. (2004). Inverted N-confused porphyrin dimer. Angewandte Chemie-International Edition, 43(38), 5077–5081. doi: 10.1002/anie.200460017
Jasat, A., & Dolphin, D. (1997). Expanded Porphyrins and Their Heterologs. Chemical Reviews, 97(6), 2267–2340. doi: 10.1021/cr950078b
Kiran, B., & Nguyen, M. T. (2002). Density functional studies on N-fused porphyrin. Electronic, magnetic and metal binding properties. Journal of Organometalic Chemistry, 643–644, 265–271. doi: 10.1016/S0022-328X(01)01399-7
Lash, T. D., Richter, D. T., & Shiner, C. M. (1999). Conjugated macrocycles related to the porphyrins. Part 16. Synthesis of hexa- and heptaalkyl-substituted inverted or N-confused porphyrins by the “3 + 1” methodology. Journal of Organic Chemistry, 64(21), 7973–7982. doi: 10.1021/jo991019r
Lavi, A., Weitman, H., Holmes, R. T., Smith, K. M., & Ehrenberg, B. (2002). The depth of porphyrin in a membrane and the membrane’s physical properties affect the photosensitizing efficiency. Biophysical Journal, 82(4), 2101–2110. doi: 10.1016/S0006-3495(02)75557-4
Liu, B., Li, X., Xu, X., Stèpień, M., & Chmielewski, P. J. (2013). 3-(Dialkoxy-phosphoryl)-N-confused phlorin and porphyrin. Synthesis, stereochemistry, and coordination properties. In Journal of Organic Chemistry (Vol. 78, Issue 4, pp. 1354–1364). doi: 10.1021/jo302689d
Liu, J. C., Ishizuka, T., Osuka, A., & Furuta, H. (2003). Modulation of axial coordination in N-confused porphyrin–antimony(V) dibromide complex by proton stimulus. Chemical Communications, 3(15), 1908–1909. doi: 10.1039/b301539b
Maeda, H., & Furuta, H. (2004). N-confused porphyrins as new scaffolds for supramolecular architecture. Journal of Porphyrins and Phthalocyanines, 8(1–3), 67–75. doi: 10.1142/s1088424604000052
Maeda, H., Ishikawa, Y., Matsuda, T., Osuka, A., & Furuta, H. (2003). Control of Cu(II) and Cu(III) states in N-confused porphyrin by protonation/deprotonation at the peripheral nitrogen. Journal of the American Chemical Society, 125(39), 11822–11823. doi: 10.1021/ja0356075
Maeda, H., Morimoto, T., Osuka, A., & Furuta, H. (2006). Halide-anion binding by singly and doubly N-confused porphyrins. Chemistry - An Asian Journal, 1(6), 832–844. doi: 10.1002/asia.200600182
Maeda, H., Osuka, A., & Furuta, H. (2003a). Hydrogen Bonding 1-D Chain Network of cis -Doubly N-Confused Porphyrins. Supramolecular Chemistry, 15(6), 447–450. 10.1080/1061027031000147485
Maeda, H., Osuka, A., & Furuta, H. (2003b). Trans Doubly N-Confused Porphyrins: Cu(III) Complexation and Formation of Rodlike Hydrogen-Bonding Networks. Journal of the American Chemical Society, 125(51), 15690–15691. doi: 10.1021/ja038519t
Maeda, H., Osuka, A., Ishikawa, Y., Aritome, I., Hisaeda, Y., & Furuta, H. (2003). N-confused porphyrin-bearing meso-perfluorophenyl groups: A potential agent that forms stable square-planar complexes with Cu(II) and Ag(III). Organic Letters, 5(8), 1293–1296. doi: 10.1021/ol034227l
Maity, D. K., Bell, R. L., & Truong, T. N. (2000). Mechanism and quantum mechanical tunneling effects on inner hydrogen atom transfer in free base porphyrin: A direct ab initio dynamics study. Journal of the American Chemical Society, 122(5), 897–906. doi: 10.1021/ja9925094
Mitrikas, G., Calle, C., & Schweiger, A. (2005). Asymmetric spin density distribution in the copper(II) complex of N-confused tetraphenylporphyrin: A multifrequency continuous-wave and pulse EPR study. Angewandte Chemie - International Edition, 44(21), 3301–3303. doi: 10.1002/anie.200500155
Morimoto, T., Taniguchi, S., Osuka, A., & Furuta, H. (2005). N-confused porphine. European Journal of Organic Chemistry, 18, 3887–3890. doi: 10.1002/ejoc.200500485
Ogawa, T., Furuta, H., Takahashi, M., Morino, A., & Uno, H. (2000). Synthesis and characterization of N-confused porphyrinatoantimony(V): Toward a low energy gap molecular wire. Journal of Organometallic Chemistry, 611(1–2), 551–557. doi: 10.1016/S0022-328X(00)00405-8
Rachlewicz, K., Wang, S. L., Ko, J. L., Hung, C. H., & Latos-Grazyński, L. (2004). Oxidation and Oxygenation of Iron Complexes of 2-Aza-21-carbaporphyrin. In Journal of the American Chemical Society, 126(13), 4420–4431. doi: 10.1021/ja039792y
Rachlewicz, K., Wang, S. L., Peng, C. H., Hung, C. H., & Latos-Grazński, L. (2003). Remarkable Paramagnetically Shifted 1H and 2H NMR Spectra of Iron(II) Complexes of 2-Aza-21-carbaporphyrin: An Evidence for Agostic Interaction. In Inorganic Chemistry, 42(23), 7348–7350. doi: 10.1021/ic034886u
Saito, S., & Osuka, A. (2011). Expanded porphyrins: Intriguing structures, electronic properties, and reactivities. Angewandte Chemie - International Edition, 50(19), 4342–4373. doi: 10.1002/anie.201003909
Schumacher, K.H., & Franck, B. (1989). Biomimetic Synthesis of an Inverted Porphyrinoid with Peripheral N Atoms. Angewandte Chemie International Edition in English, 28(9), 1243–1245. doi: 10.1002/anie.198912431
Sessler, J. L. (1994). New Porphyrin Isomers. Angewandte Chemie International Edition in English, 33(13), 1348–1350. doi: 10.1002/anie.199413481
Sessler, J. L., Brucker, E. A., Weghorn, S. J., Kisters, M., Schäfer, M., Lex, J., & Vogel, E. (1994). Corrphycene: A New Porphyrin Isomer. Angewandte Chemie International Edition in English, 33(22), 2308–2312. doi: 10.1002/anie.199423081
Shin, J., Furuta, H., & Osuka, A. (2001). N-Fused Pentaphyrin. Angewandte Chemie, 113(3), 639–641. 10.1002/1521-3757(20010202)113:3<639::AID-ANGE639>3.0.CO;2-3
Shin, J., Furuta, H., Yoza, K., Igarashi, S., & Osuka, A. (2001). meso -Aryl-Substituted Expanded Porphyrins. Journal of the American Chemical Society, 123(29), 7190–7191. doi: 10.1021/ja0106624
Skorey, K. I., & Brown, R. S. (1986). Correction. Biomimetic Models for Cysteine Proteases. 2. Nucleophilic Thiolate-Containing Zwitterions Produced from Imidazole-Thiol Pairs. A Model for the Acylation Step in Papain-Mediated Hydrolyses. Journal of the American Chemical Society, 108(25), 8119–8119. doi: 10.1021/ja00285a600
Srinivasan, A., & Furuta, H. (2005). Confusion approach to porphyrinoid chemistry. Accounts of Chemical Research, 38(1), 10–20. doi: 10.1021/ar0302686
Srinivasan, A., Toganoh, M., Niino, T., Osuka, A., & Furuta, H. (2008). Synthesis of N-confused tetraphenylporphyrin rhodium complexes having versatile metal oxidation states. Inorganic Chemistry, 47(23), 11305–11313. doi: 10.1021/ic061093+
Sternberg, E. D., Dolphin, D., & Brückner, C. (1998). Porphyrin-based photosensitizers for use in photodynamic therapy. Tetrahedron, 54(17), 4151–4202. 10.1016/S0040-4020(98)00015-5
Stone, A., & Fleischer, E. B. (1968). The molecular and crystal structure of porphyrin diacids. Journal of the American Chemical Society, 90(11), 2735–2748. doi: 10.1021/ja01013a001
Suzuki, M., Yoon, M. C., Kim, D. Y., Kwon, J. H., Furuta, H., Kim, D., & Osuka, A. (2006). A new entry to doubly N-confused [26]hexaphyrins(1.1.1.1.1.1) from normal [26]hexaphyrins(1.1.1.1.1.1) through an unprecedented double pyrrolic rearrangement. Chemistry - A European Journal, 12(6), 1754–1759. doi: 10.1002/chem.200501061
Szterenberg, L., & Latos-Grazyński, L. (1997). Structure and stability of 2-Aza-21-carbaporphyrin tautomers prearranged for coordination. Inorganic Chemistry, 36(27), 6287–6291. doi: 10.1021/ic9705857
Szyszko, B., & Latos-Grazyński, L. (2015). Core chemistry and skeletal rearrangements of porphyrinoids and metalloporphyrinoids. Chemical Society Reviews, 44(11), 3588–3616. doi: 10.1039/c4cs00398e
Toganoh, M., Ishizuka, T., & Furuta, H. (2004). Synthesis and properties of rhenium tricarbonyl complex bearing N-fused tetraphenylporphyrin ligand. Chemical Communications, 21, 2464–2465. doi: 10.1039/b406234e
Ulman, A., Manassen, J., Frolow, F., & Rabinovich, D. (1978). Synthesis of new tetraphenylporphyrin molecules containing heteroatoms other than nitrogen. III. Tetraphenyl-21-tellura-23-thiaporphyrin: an internally-bridged porphyrin. Tetrahedron Letters, 19(21), 1885–1886. doi: 10.1016/S0040-4039(01)94699-4
Vogel, E., Köcher, M., Schmickler, H., & Lex, J. (1986). Porphycene-a Novel Porphin Isomer. Angewandte Chemie International Edition in English, 25(3), 257–259. doi: 10.1002/anie.198602571
Vogel, E., Scholz, P., Demuth, R., Erben, C., Bröring, M., Schmickler, H., Lex, J., Hohlneicher, G., Bremm, D., & Wu, Y. D. (1999). Isoporphycene: The fourth constitutional lsomet of porphyrin with an N4 core-occurrence of E/Z isomerism. Angewandte Chemie-International Edition, 38(19), 2919–2923. doi: 10.1002/(SICI)1521-3773(19991004)38:19<2919::AID-ANIE2919>3.0.CO;2-W
Ziegler, C. J., Erickson, N. R., Dalby, M. R., & Nemykin, V. N. (2013). Magnetic circular dichroism spectroscopy of N-confused porphyrin and its ionized forms. In Journal of Physical Chemistry A, 117(45), 11499–11508). doi: 10.1021/jp409013d