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Siamese-Twin Porphyrin Origami: Oxidative Fusing and Folding

机译：暹罗双卟啉折纸：氧化融合和折叠

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摘要

Oxidation of a nonaromatic Siamese-twin porphyrin, a pyrazole-containing expanded porphyrin with two porphyrinlike binding pockets, with a stoichiometric amount of the two-electron, two-proton oxidizing agent 2,3-dichloro-5,6-dicyano-1,4-benzochinone led to the formation of a single N-pz-Co-Ph linkage between the pyrazole unit with a neighboring meso-phenyl group, forming a pyrazolo- [1,5-a]indole moiety. Repeated treatment with a second equivalent of the oxidant yielded a doubly N-fused species, involving the second pyrazole moiety. The conversion products were characterized by variable-temperature and multinuclear 1D and 2DNMR spectroscopy. The fusions strongly alter the conformation of the macrocycles, as shown by X-ray diffraction analyses of all three compounds, eventually leading to a folded structure. UV/Vis and NMR-spectroscopic investigations indicated the presence of highly delocalized but nonmacrocycle-aromatic systems. This behavior of the Siamese-twin porphyrin in response to oxidation is in contrast to the behavior of related all-pyrrole-based expanded macrocycles that switch, by redox processes and protonation, between Huckel and Mobius aromatic states.
机译：氧化非芳族连体双卟啉，一种带有两个卟啉样结合袋的含吡唑的膨胀卟啉，化学计量的二电子，二质子氧化剂2,3-dichloro-5,6-dicyano-1， 4-苯甲酮导致吡唑单元与相邻的内消旋苯基之间形成单个N-pz-Co-Ph键，形成吡唑并[1,5-a]吲哚部分。用第二当量的氧化剂进行重复处理产生了一个双氮稠合的物质，涉及第二吡唑部分。通过可变温度和多核一维和二维核磁共振波谱对转化产物进行表征。融合强烈地改变了大环的构象，如对所有三种化合物的X射线衍射分析所示，最终导致了折叠结构。 UV / Vis和NMR光谱研究表明存在高度离域但非大环芳烃系统。连体双卟啉响应氧化的这种行为与相关的基于全吡咯的膨胀大环的行为形成对比，后者通过氧化还原过程和质子化在Huckel和Mobius芳族状态之间切换。

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