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A Benzodipyrrole-Derived Sapphyrin
Panda, Pradeepta K,Kang, Young-Jin,Lee, Chang-Hee WILEY-VCH Verlag 2005 Angewandte Chemie. international edition Vol.44 No.26
<B>Graphic Abstract</B> <P>Within the framework: The fused benzodipyrrole unit within the sapphyrin 1 has a significant influence on its structure as compared to those of usual sapphyrins. The fused benzene ring partly inhibits distortion of the macrocycle about the dipyrrole unit (see structure of 1⋅2 H<SUP>+</SUP> 2 (p-CH<SUB>3</SUB>C<SUB>6</SUB>H<SUB>4</SUB>SO<SUB>3</SUB><SUP>−</SUP>); C gray, N blue, O red, S yellow) and contributes to the significant red-shift of Q-bands. <img src='wiley_img/14337851-2005-44-26-ANIE200500944-content.gif' alt='wiley_img/14337851-2005-44-26-ANIE200500944-content'> </P>
Kee, Se-Young,Lim, Jong Min,Kim, Soo-Jin,Yoo, Jaeduk,Park, Jung-Su,Sarma, Tridib,Lynch, Vincent M.,Panda, Pradeepta K.,Sessler, Jonathan L.,Kim, Dongho,Lee, Chang-Hee Royal Society of Chemistry 2011 Chemical communications Vol.47 No.24
<P>Two new expanded porphyrins, naphthorubyrin and naphthosapphyrin, were synthesized. The π-extended rubyrin was isolated and structurally characterized in its monoprotonated form. The sapphyrin congener undergoes pyrrole inversion as a function of the protonation state. These conformational effects are reflected in the spectroscopic features, including the excited singlet state lifetimes.</P> <P>Graphic Abstract</P><P>Two new expanded porphyrins, naphthorubyrin and naphthosapphyrin, have been synthesized. <IMG SRC='http://pubs.rsc.org/services/images/RSCpubs.ePlatform.Service.FreeContent.ImageService.svc/ImageService/image/GA?id=c1cc11733e'> </P>
Ishida, Masatoshi,Kim, Soo-Jin,Preihs, Christian,Ohkubo, Kei,Lim, Jong Min,Lee, Byung Sun,Park, Jung Su,Lynch, Vincent M.,Roznyatovskiy, Vladimir V.,Sarma, Tridib,Panda, Pradeepta K.,Lee, Chang-Hee,Fu Nature Publishing Group 2013 Nature chemistry Vol.5 No.1
Proton-coupled electron transfer (PCET) processes are among the most important phenomena that control a variety of chemical and biological transformations. Although extensively studied in a variety of natural systems and discrete metal complexes, PCET mechanisms are less well codified in the case of purely organic compounds. Here we report that a planar 棺,棺??phenylene-bridged hexaphyrin (1.0.1.0.1.0), a 24 ?-electron antiaromatic species termed rosarin, displays unique redox reactivity on protonation. Specifically, treatment with acid (for example, HI) yields a 26 ?-electron aromatic triprotonated monocationic species that is produced spontaneously via an intermediate??but stable??25 ?-electron non-aromatic triprotonated monoradical dication. This latter species is also produced on treatment of the original 24 ?-electron antiaromatic starting material with HCl or HBr. The stepwise nature of the proton-coupled reduction observed in the planar rosarin stands in marked contrast to that seen for non-annulated rosarins and other ostensibly antiaromatic expanded porphyrinoids.