- Novel Versatile Synthesis of Substituted Tetrabenzoporphyrins
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A novel general synthetic route to tetraaryltetrabenzoporphyrins (Ar 4TBP) with various peripheral functional groups is developed. The procedure includes (i) Barton-Zard condensation of 1-nitro- or 1-phenylsulfonylcyclohexenes with isocyanoacet
- Finikova, Olga S.,Cheprakov, Andrei V.,Beletskaya, Irina P.,Carroll, Patrick J.,Vinogradov, Sergei A.
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- Electrochemistry of nonplanar copper(II) tetrabutano- and tetrabenzotetraarylporphyrins in nonaqueous media
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Two series of copper tetraarylporphyrins containing β,β′-fused tetrabutano or tetrabenzo groups were synthesized and characterized as to their electrochemistry and spectroelectrochemistry in nonaqueous media. The examined compounds are represented as butano-(TpYPP)CuII and benzo-(TpYPP)CuII, where TpYPP is the porphyrin dianion and Y is a CH3, H or Cl substituent on the para-position of the four meso-phenyl rings of the compound. Each neutral porphyrin in the two series is ESR active and shows a typical d9 Cu(ii) signal in frozen CH2Cl2 solution. Each Cu(ii) porphyrin also undergoes two reversible one-electron reductions and two reversible one-electron oxidations in DMF or CH2Cl2 containing 0.1 M tetra-n-butylammonium perchlorate to give a π-anion radical and dianion upon reduction and a π-cation radical and dication upon oxidation. A third one-electron oxidation is also observed for butano-(TpYPP)Cu (Y = CH3 and H) and benzo-(TPP)Cu in PhCN and this process is assigned to the CuII/CuIII transition. The reversible half-wave potential for the first oxidation of each compound in both series is shifted negatively by about 500 mV as compared to E1/2 values for oxidation of the related copper tetraarylporphyrin without the four fused benzo or butano rings while smaller positive shifts of 60 and 300 mV are seen for reduction of the tetrabenzotetraarylporphyrins and tetrabutaotetraarylporphyrins, respectively, as compared to the same redox reactions of the related tetraarylporphyrins. The electrochemically measured HOMO-LUMO gap averages 1.76 ± 0.05 V for benzo-(TpYPP)CuII, 2.04 ± 0.06 V for butano-(TpYPP)CuII and 2.33 ± 0.03 for (TpYPP)Cu in CH2Cl2.
- Ye, Lina,Ou, Zhongping,Fang, Yuanyuan,Xue, Songlin,Song, Yang,Wang, Liping,Wang, Mengli,Kadish, Karl M.
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- Highly efficient, near-infrared electrophosphorescence from a Pt-metalloporphyrin complex
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(Graph Presented) Red-shifting beyond red: The nonplanar porphyrin complex [Pt(tpbp)] (tpbp = tetraphenyltetrabenzoporphyrin) has been used as a phosphorescent dopant in highly efficient electrophosphorescent devices that emit in the near-infrared region
- Borek, Carsten,Hanson, Kenneth,Djurovich, Peter I.,Thompson, Mark E.,Aznavour, Kristen,Bau, Robert,Sun, Yiru,Forrest, Stephen R.,Brooks, Jason,Michalski, Lech,Brown, Julie
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- Retooling manganese(III) porphyrin-based peroxynitrite decomposition catalysts for selectivity and oral activity: A potential new strategy for treating chronic pain
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Redox-active metalloporphyrins represent the most well-characterized class of catalysts capable of attenuating oxidative stress in vivo through the direct interception and decomposition of superoxide and peroxynitrite. While many interesting pharmacologic
- Rausaria, Smita,Ghaffari, Mahsa M.E.,Kamadulski, Andrew,Rodgers, Kenny,Bryant, Leesa,Chen, Zhoumou,Doyle, Tim,Shaw, Michael J.,Salvemini, Daniela,Neumann, William L.
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supporting information; experimental part
p. 8658 - 8669
(2012/02/16)
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