Preparation and spectroscopic properties of pure tetrabenzoporphyrins

Koehorst, R.B.M.; Kleibeuker, Joop F.; Schaafsma, T.J.; Bie, D. A. De; Geurtsen, Bart; Henrie, Robert N.; Plas, H. C. Van Der

doi:10.1039/p29810001005

Cited by 33 publications

(23 citation statements)

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“…The shoulder peaks greatly increased when the solvent was changed to 5 % pyridine/THF. TBP 2a in a 5 % pyridine/THF solution had obvious split Soret bands at 412 and 427 nm corresponding to B y and B x [21] with similar molar extinction coefficients, and a fused Q-I band at 661 nm as reported by Koehorst et al [22] In the UV spectra of tribenzoporphyrins (Figure 3c), proportional bathochromic shifts were observed as the number of sulfur atoms increased. In the spectra of thiatribenzoporphyrins 10b,c, new absorption bands with very long wavelengths were observed at 724 (log 10 ε = 2.96) and 750 (2.99) nm, respectively.…”

Section: Spectroscopic Analyses Of the Porphyrinssupporting

confidence: 55%

Thermal Behavior of Free‐Base and Core‐Modified Bicyclo[2.2.2]octadiene‐Fused Porphyrins

et al. 2007

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Multistep thermal fragmentation of quadruply bicyclo[2.2.2]-octadiene-fused porphyrins giving tetrabenzoporphyrins was examined in detail. After the first extrusion of an ethylene molecule from the porphyrin derivative, the opposite bicyclo-[2.2.2]octadiene moiety preferentially underwent the second retro-Diels-Alder reaction to give an opp-dibenzoporphyrin derivative rather than an adj-dibenzoporphyrin derivative. These two benzoporphyrin derivatives then decomposed to give a tribenzoporphyrin derivative in similar rates. The temperature regions of these fragmentations could not be distinguished by thermogravimetric analysis. In contrast, the third and the fourth fragmentations obviously occurred stepwise. There was a temperature region where the tribenzoporphy-

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Section: Spectroscopic Analyses Of the Porphyrinssupporting

confidence: 55%

Thermal Behavior of Free‐Base and Core‐Modified Bicyclo[2.2.2]octadiene‐Fused Porphyrins

et al. 2007

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“…The Zn 2 + was removed [12] with H 2 SO 4 , and the metals were incorporated into H 2 -TBP using dimethylformamide (DMF) for Cd(II), Cu(II) [22], pyridine for Ni(II) [18], benzonitrile for VO(IV), and magnesium hexapyridine diiodide for Mg(II) [15]. These complexes were purified on thin layer silica gel plates using methanol/chloroform/pyridine mixtures as the elutants.…”

Section: Experimental*mentioning

confidence: 99%

“…A one-pot template method now yields gram quantities of Zn-TBP [7], and both ring [8] and meso-substituted species [9,10] have been prepared. Recent work has appeared on Fe [11], Pt [12,13], Pd [12], Zn [6,14], Cd [15], Mg [15], Co [16] and Ge [16] complexes, and ring-oxidized M-TBP iodides [17,18], where M stands for a metal. The spectrum of Mg-TBP resembles that of chlorophyll [19] and it has been suggested [20] that both H 2 -TBP and Mg-TBP(py) 2 , where py stands for pyridine (as well as the chlorin of porphin [21]) are constituents of interstellar dust.…”

Section: Introductionmentioning

confidence: 99%

Tetrabenzoporphyrins: Metal Incorporation and Exchange Kinetics, Ligational Equilibria and Pulse Radiolysis Studies

Cromer

Hambright

Grodkowski

et al. 1997

J. Porphyrins Phthalocyanines

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The solution chemistry of tetrabenzoporphyrin ( TBP ) and several of its metal derivatives were compared with that of the corresponding octaethylporphyrins. Kinetic studies were done on zinc and cadmium ion incorporation and the exchange reactions of cadmium porphyrins with zinc. Formation constants of Cd (II), Cu (II), VO (IV), Ni (II), Zn (II) and Mg (II) porphyrins with pyridine were determined for both compounds. The spectra of the radical cations of Ni (II), Mg (II) and H 2- TBP were obtained, as well as that of the radical anion of Mg (II)- TBP . Aside from the new Ni (I)- TBP , no long-lived intermediates, as noted with other porphyrins, were observed upon reduction of the tetrabenzoporphyrins. The low basicity and rigidity of the tetrabenzoporphyrin nucleus may explain many of its relative reactivity properties.

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“…Tetrabenzoporphyrin (TBP) is often considered an intermediate class between porphyrins and phthalocyanines. 113 The unsubstituted tetrabenzoporphyrin can be obtained starting from phthalic anhydride 150 which can be converted to 151, followed by heating in aqueous ammonia to form the phthalimide derivative 152. Condensation of 152 in the presence of zinc acetate forms the symmetric TBP 153.…”

Section: Tetrabenzoporphyrinsmentioning

confidence: 99%