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Volumn 14, Issue 11, 2011, Pages 1827-1832

Substitution effects on the UV-vis and 1H NMR spectra of the dications of meso and/or β substituted porphyrins with trifluoroacetic acid: Electron-deficient porphyrins compared to the electron-rich ones

Author keywords

Ab initio and DFT calculations; Nonplanar porphyrins; Porphyrin dications; Q(0,0) band; Soret band

Indexed keywords


EID: 80053575641     PISSN: 13877003     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.inoche.2011.08.019     Document Type: Article
Times cited : (36)

References (44)
  • 1
    • 33746835192 scopus 로고
    • The molecular and crystal structure of porphyrin diacids
    • A. Stone, and E.B. Fleischer The molecular and crystal structure of porphyrin diacids J. Am. Chem. Soc. 90 1968 2735 2748
    • (1968) J. Am. Chem. Soc. , vol.90 , pp. 2735-2748
    • Stone, A.1    Fleischer, E.B.2
  • 2
    • 0000324445 scopus 로고
    • Substituent effects in noncoplanar π systems. ms-porphins
    • M. Meot-Ner, and A.D. Adler Substituent effects in noncoplanar π systems. ms-porphins J. Am. Chem. Soc. 97 1975 5107 5111
    • (1975) J. Am. Chem. Soc. , vol.97 , pp. 5107-5111
    • Meot-Ner, M.1    Adler, A.D.2
  • 4
    • 0034143066 scopus 로고    scopus 로고
    • Exclusive 2:1 molecular complexation of 2,3-dichloro-5,6-dicyano- benzoquinone and para-substituted meso-tetraphenylporphyrins: Spectral analogues for diprotonated meso-tetraphenylporphyrin
    • D. Mohajer, and H. Dehghani Exclusive 2: 1 molecular complexation of 2,3-dichloro-5,6-dicyanobenzoquinone and para-substituted meso- tetraphenylporphyrins: spectral analogues for diprotonated meso- tetraphenylporphyrin J. Chem. Soc. Perkin Trans. 2 2000 199 205 (Pubitemid 35165991)
    • (2000) Journal of the Chemical Society. Perkin Transactions 2 , Issue.2 , pp. 199-205
    • Mohajer, D.1    Dehghani, H.2
  • 5
    • 0033929778 scopus 로고    scopus 로고
    • Preparation and spectroscopic characterization of 2:1 molecular complexes of tetracyanoethylene and meso-tetraphenylporphyrins
    • DOI 10.1246/bcsj.73.1477
    • D. Mohajer, and H. Dehghani Preparation and spectroscopic characterization of 2:1 molecular complexation of tetracyanoethelene and meso-tetraphenylporphyrins Bull. Chem. Soc. Jpn. 73 2000 1477 1484 (Pubitemid 30490188)
    • (2000) Bulletin of the Chemical Society of Japan , vol.73 , Issue.7 , pp. 1477-1484
    • Mohajer, D.1    Dehghani, H.2
  • 6
    • 0039015952 scopus 로고    scopus 로고
    • +-porphyrindiium salts (dication salts)
    • +-porphyrindiium salts (dication salts) Z. Naturforsch 55b 2000 336 344
    • (2000) Z. Naturforsch , vol.55 B , pp. 336-344
    • Senge, M.O.1
  • 8
    • 34347206693 scopus 로고    scopus 로고
    • Interaction of para-substituted meso-tetraphenylporphyrins and meso-tetra(n-propyl)porphyrin with weak and strong carboxylic acids: A UV-Vis spectroscopic study
    • S. Zakavi, and N.G. Gharab Interaction of para-substituted meso-tetraphenylporphyrins and meso-tetra(n-propyl)porphyrin with weak and strong carboxylic acids: a UV-Vis spectroscopic study Polyhedron 26 2007 2425 2432
    • (2007) Polyhedron , vol.26 , pp. 2425-2432
    • Zakavi, S.1    Gharab, N.G.2
  • 9
    • 37549049018 scopus 로고    scopus 로고
    • Core protonation of meso-tetraphenylporphyrin with tetrafluoroboric acid: Unusual water-mediated hydrogen bonding of H4t pp 2+ to the counterion
    • S. Rayati, S. Zakavi, A. Ghaemi, and P.J. Carroll Core protonation of meso-tetraphenylporphyrin with tetrafluoroboric acid: unusual water-mediated hydrogen bonding of H4t pp 2+ to the counterion Tetrahedron Lett. 49 2008 664 667
    • (2008) Tetrahedron Lett. , vol.49 , pp. 664-667
    • Rayati, S.1    Zakavi, S.2    Ghaemi, A.3    Carroll, P.J.4
  • 11
    • 0001241107 scopus 로고
    • Perchloric acid titrations of porphyrins in nitrobenzene
    • S. Aronoff Perchloric acid titrations of porphyrins in nitrobenzene J. Phys. Chem. 62 1958 428 431
    • (1958) J. Phys. Chem. , vol.62 , pp. 428-431
    • Aronoff, S.1
  • 12
    • 0000437578 scopus 로고
    • Sequential protonation of meso-(p-(dimethy1amino)phenyl)porphyrins: Charge-transfer excited states producing hyperporphyrin
    • R.I. Walter, E.C.A. Ojadi, and H. Linschitz Sequential protonation of meso-(p-(dimethy1amino)phenyl)porphyrins: charge-transfer excited states producing hyperporphyrin J. Phys. Chem. 97 1993 13192 13197
    • (1993) J. Phys. Chem. , vol.97 , pp. 13192-13197
    • Walter, R.I.1    Ojadi, E.C.A.2    Linschitz, H.3
  • 13
    • 33947295521 scopus 로고
    • Structure of porphyrins and metalloporphyrins
    • E.B. Fleischer Structure of porphyrins and metalloporphyrins Acc. Chem. Res. 3 1970 105 112
    • (1970) Acc. Chem. Res. , vol.3 , pp. 105-112
    • Fleischer, E.B.1
  • 14
    • 0007016836 scopus 로고
    • On the planarity and resonance effect of tetraphenylporphyren and its metallocomplexes
    • A. Wolberg On the planarity and resonance effect of tetraphenylporphyren and its metallocomplexes J. Mol. Struct. 21 1974 61 66
    • (1974) J. Mol. Struct. , vol.21 , pp. 61-66
    • Wolberg, A.1
  • 15
    • 37049116599 scopus 로고
    • The molecular structure of the diacid species of αβγ δ-tetra-4-pyridylporphine and αβγδ- tetraphenylporphine
    • E.B. Fleischer, and A. Stone The molecular structure of the diacid species of αβγδ-tetra-4-pyridylporphine and αβγδ-tetraphenylporphine Chem. Commun. 1967 332 333
    • (1967) Chem. Commun. , pp. 332-333
    • Fleischer, E.B.1    Stone, A.2
  • 17
    • 38649139361 scopus 로고    scopus 로고
    • Pure manganese(III) 5,10,15,20-tetrakis(4-benzoic acid)porphyrin (MnTBAP) is not a superoxide dismutase mimic in aqueous systems: A case of structure-activity relationship as a watchdog mechanism in experimental therapeutics and biology
    • J.S. Rebouças, I. Spasojević, and I. Batinić-Haberle Pure manganese(III) 5,10,15,20-tetrakis(4-benzoic acid)porphyrin (MnTBAP) is not a superoxide dismutase mimic in aqueous systems: a case of structure-activity relationship as a watchdog mechanism in experimental therapeutics and biology J. Biol. Inorg. Chem. 13 2008 289 302
    • (2008) J. Biol. Inorg. Chem. , vol.13 , pp. 289-302
    • Rebouças, J.S.1    Spasojević, I.2    Batinić-Haberle, I.3
  • 19
    • 61849138035 scopus 로고
    • The electrochemistry of metalloporphyrins in nonaqueous media
    • K.M. Kadish The electrochemistry of metalloporphyrins in nonaqueous media Prog. Inorg. Chem. 34 1986 435 605
    • (1986) Prog. Inorg. Chem. , vol.34 , pp. 435-605
    • Kadish, K.M.1
  • 21
    • 0346559771 scopus 로고
    • Nonplanar porphyrins. X-ray structures of (2,3,7,8,12,13,17,18-octaethyl- and -octamethyl-5,10,15,20-tetraphenylporphinato)zinc(II)
    • K.M. Barkigia, M.D. Berber, J. Fajer, C.J. Medforth, M.W. Renner, and K.M. Smith Nonplanar porphyrins. X-ray structures of (2,3,7,8,12,13,17,18- octaethyl- and -octamethyl-5,10,15,20-tetraphenylporphinato)zinc(II) J. Am. Chem. Soc. 112 1990 8851 8857
    • (1990) J. Am. Chem. Soc. , vol.112 , pp. 8851-8857
    • Barkigia, K.M.1    Berber, M.D.2    Fajer, J.3    Medforth, C.J.4    Renner, M.W.5    Smith, K.M.6
  • 23
    • 33845283431 scopus 로고
    • Electrochemical polymerization of amino-, pyrrole-, and hydroxy-substituted tetraphenylporphyrins
    • A. Bettelheim, B.A. White, S.A. Raybuck, and R.W. Murray Electrochemical polymerization of amino-, pyrrole-, and hydroxy-substituted tetraphenylporphyrins Inorg. Chem. 26 1987 1009 1017
    • (1987) Inorg. Chem. , vol.26 , pp. 1009-1017
    • Bettelheim, A.1    White, B.A.2    Raybuck, S.A.3    Murray, R.W.4
  • 24
    • 0042813364 scopus 로고
    • Spectra of porphyrins
    • M. Gouterman Spectra of porphyrins J. Mol. Spectrosc. 6 1961 138 163
    • (1961) J. Mol. Spectrosc. , vol.6 , pp. 138-163
    • Gouterman, M.1
  • 25
    • 0001663368 scopus 로고
    • A proton NMR study of the reactions with acid of meso- tetraphenylporphyrins with various numbers of 4-dimethylamino groups
    • R.I. Walter, E.C.A. Ojadi, and H. Linschitzll A proton NMR study of the reactions with acid of meso-tetraphenylporphyrins with various numbers of 4-dimethylamino groups J. Phys. Chem. 97 1993 13308 13312
    • (1993) J. Phys. Chem. , vol.97 , pp. 13308-13312
    • Walter, R.I.1    Ojadi, E.C.A.2    Linschitzll, H.3
  • 27
    • 0000319034 scopus 로고    scopus 로고
    • Supramolecular Multiporphyrin Architecture. Coordination Polymers and Open Networks in Crystals of Tetrakis(4-cyanophenyl)- and Tetrakis(4- nitrophenyl)metalloporphyrin
    • R.K. Kumar, S. Balasubramanian, and I. Goldberg Supramolecular multiporphyrin architecture. Coordination polymers and open networks in crystals of tetrakis(4-cyanophenyl)- and tetrakis(4-nitrophenyl)metalloporphyrin Inorg. Chem. 37 1998 541 552 (Pubitemid 128496639)
    • (1998) Inorganic Chemistry , vol.37 , Issue.3 , pp. 541-552
    • Kumar, R.K.1    Balasubramanian, S.2    Goldberg, I.3
  • 29
    • 33748514809 scopus 로고    scopus 로고
    • Synthesis of 3,4-diarylpyrroles and conversion into dodecaarylporphyrins; a new approach to porphyrins with altered redox potentials
    • N. Ono, H. Miyagawa, T. Ueta, T. Ogawa, and H. Tani Synthesis of 3,4-diarylpyrroles and conversion into dodecaarylporphyrins; a new approach to porphyrins with altered redox potentials J. Chem. Soc. Perkin Trans. 1 1998 1595 1601 (Pubitemid 128756902)
    • (1998) Journal of the Chemical Society - Perkin Transactions 1 , Issue.10 , pp. 1595-1601
    • Ono, N.1    Miyagawa, H.2    Ueta, T.3    Ogawa, T.4    Tani, H.5
  • 30
    • 79955806804 scopus 로고    scopus 로고
    • Comparative study of catalytic activity of some biomimetic models of cytochrome P450 in oxidation of olefins with tetra-n-butylammonium periodate: Electron-rich Mn-porphyrins versus the electron-deficient ones
    • S. Zakavi, F. Heidarizadi, and S. Rayati Comparative study of catalytic activity of some biomimetic models of cytochrome P450 in oxidation of olefins with tetra-n-butylammonium periodate: electron-rich Mn-porphyrins versus the electron-deficient ones Inorg. Chem. Commun. 14 2011 1010 1013
    • (2011) Inorg. Chem. Commun. , vol.14 , pp. 1010-1013
    • Zakavi, S.1    Heidarizadi, F.2    Rayati, S.3
  • 31
    • 79956360124 scopus 로고    scopus 로고
    • Substitution effects on the catalytic activity of Mn(III)-porphyrins in epoxidation of alkenes with iodosylbenzene: A comparison between the electron-rich and electron-deficient porphyrins
    • S. Zakavi, and L. Ebrahimi Substitution effects on the catalytic activity of Mn(III)-porphyrins in epoxidation of alkenes with iodosylbenzene: a comparison between the electron-rich and electron-deficient porphyrins Polyhedron 30 2011 1732 1738
    • (2011) Polyhedron , vol.30 , pp. 1732-1738
    • Zakavi, S.1    Ebrahimi, L.2
  • 32
    • 0037903258 scopus 로고    scopus 로고
    • An improved protocol for the synthesis of antipodal β-tetrabromo- tetraphenylporphyrin and the crystal structure of its Zn(II) complex
    • DOI 10.1016/S0040-4039(03)01143-2
    • P.K. Kumar, P. Bhyrappa, and B. Varghese An improved protocol for the synthesis of antipodal β-tetrabromo-tetraphenylporphyrin and the crystal structure of its Zn(II) complex Tetrahedron Lett. 44 2003 4849 4851 (Pubitemid 36694251)
    • (2003) Tetrahedron Letters , vol.44 , Issue.26 , pp. 4849-4851
    • Kumar, P.K.1    Bhyrappa, P.2    Varghese, B.3
  • 34
    • 71549136487 scopus 로고    scopus 로고
    • Thienyl-appended porphyrins: Synthesis, photophysical and electrochemical properties, and their applications
    • N.M. Boyle, J. Rochford, and M.T. Pryce Thienyl-appended porphyrins: synthesis, photophysical and electrochemical properties, and their applications Coord. Chem. Rev. 254 2010 77 102
    • (2010) Coord. Chem. Rev. , vol.254 , pp. 77-102
    • Boyle, N.M.1    Rochford, J.2    Pryce, M.T.3
  • 35
    • 34249278104 scopus 로고    scopus 로고
    • Effects of porphyrin composition on the activity and selectivity of the iron(III) porphyrin catalysts for the epoxidation of cyclooctene by hydrogen peroxide
    • DOI 10.1016/j.molcata.2007.03.030, PII S1381116907001926
    • N.A. Stephenson, and A.T. Bell Effects of porphyrin composition on the activity and selectivity of the iron(III) porphyrin catalysts for the epoxidation of cyclooctene by hydrogen peroxide J. Mol. Catal. A: Chem. 272 2007 108 117 (Pubitemid 46809595)
    • (2007) Journal of Molecular Catalysis A: Chemical , vol.272 , Issue.1-2 , pp. 108-117
    • Stephenson, N.A.1    Bell, A.T.2
  • 37
    • 0002248132 scopus 로고
    • Recent advances in the stereochemistry of metallotetrapyrroles
    • W.R. Scheidt, and Y.J. Lee Recent advances in the stereochemistry of metallotetrapyrroles Struct. Bonding, Berlin 64 1987 1 70
    • (1987) Struct. Bonding, Berlin , vol.64 , pp. 1-70
    • Scheidt, W.R.1    Lee, Y.J.2
  • 38
    • 0031627376 scopus 로고    scopus 로고
    • Luminescence and structure of the protonated forms of meso-tetraarylporphyrins in solution
    • V.N. Knyukshto, K.N. Solovyov, and G.D. Egorova Luminescence and structure of the protonated forms of meso-tetraarylporphyrins in solution Biospectroscopy 4 1998 121 133 (Pubitemid 128761397)
    • (1998) Biospectroscopy , vol.4 , Issue.2 , pp. 121-133
    • Knyukshto, V.N.1    Solovyov, K.N.2    Egorova, G.D.3
  • 39
    • 0001104652 scopus 로고
    • An MO study of organic sulfur compounds. Comparison with the corresponding oxygen compounds
    • T. Matsushita, Y. Osamura, N. Misawa, K. Nishimoto, and Y. Tsuno An MO study of organic sulfur compounds. Comparison with the corresponding oxygen compounds Bull. Chem. Soc. Jpn. 52 1979 2521 2526
    • (1979) Bull. Chem. Soc. Jpn. , vol.52 , pp. 2521-2526
    • Matsushita, T.1    Osamura, Y.2    Misawa, N.3    Nishimoto, K.4    Tsuno, Y.5
  • 40
    • 33751391001 scopus 로고
    • Beta-halogenated-pyrrole porphyrins. Molecular structures of 2,3,7,8,12,13,17,18-octabromo-5,10,15,20-tetramesitylporphyrin, nickel(II) 2,3,7,8,12,13,17,18-octabromo-5,10,15,20-tetramesitylporphyrin, and nickel(II) 2,3,7,8,12,13,17,18-octabromo-5,10,15,20-tetrakis(pentafluorophenyl)porphyrin
    • D. Mandon, P. Ochenbein, J. Fischer, R. Weiss, K. Jayaraj, R.N. Austin, A. Gold, P.S. White, and O. Brigaud Beta-halogenated-pyrrole porphyrins. Molecular structures of 2,3,7,8,12,13,17,18-octabromo-5,10,15,20- tetramesitylporphyrin, nickel(II) 2,3,7,8,12,13,17,18-octabromo-5,10,15,20- tetramesitylporphyrin, and nickel(II) 2,3,7,8,12,13,17,18-octabromo-5,10,15,20- tetrakis(pentafluorophenyl)porphyrin Inorg. Chem. 31 1992 2044 2049
    • (1992) Inorg. Chem. , vol.31 , pp. 2044-2049
    • Mandon, D.1    Ochenbein, P.2    Fischer, J.3    Weiss, R.4    Jayaraj, K.5    Austin, R.N.6    Gold, A.7    White, P.S.8    Brigaud, O.9
  • 41
    • 4243539377 scopus 로고
    • Electronic structure calculations on workstation computers: The program system Turbomole
    • R. Ahlrichs, M. Bär, M. Häser, H. Horn, and C. Kölmel Electronic structure calculations on workstation computers: the program system Turbomole Chem. Phys. Lett. 162 1989 165 169
    • (1989) Chem. Phys. Lett. , vol.162 , pp. 165-169
    • Ahlrichs, R.1    Bär, M.2    Häser, M.3    Horn, H.4    Kölmel, C.5
  • 42
    • 70350415342 scopus 로고    scopus 로고
    • V6.0 Forschungszentrum Karlsruhe GmbH, TURBOMOLE GmbH
    • TURBOMOLE. V6.0 Forschungszentrum Karlsruhe GmbH, TURBOMOLE GmbH. 2009.
    • (2009) TURBOMOLE
  • 44
    • 7444247675 scopus 로고
    • Electronic consequences of nonplanar core conformations in electron-deficient porphyrins: The structure and spectroscopic properties of [5,10,15,20-tetrakis(heptafluoropropyl)-porphinato]cobalt(II)
    • S.G. DiMagno, A.K. Wertsching, and C.R. Ross Electronic consequences of nonplanar core conformations in electron-deficient porphyrins: the structure and spectroscopic properties of [5,10,15,20-tetrakis(heptafluoropropyl)-porphinato] cobalt(II) J. Am. Chem. Soc. 117 1995 8279 8280
    • (1995) J. Am. Chem. Soc. , vol.117 , pp. 8279-8280
    • Dimagno, S.G.1    Wertsching, A.K.2    Ross, C.R.3


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