Expanded Rosarin: A Versatile Fullerene (C60) Receptor,Journal of the American Chemical Society

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Expanded Rosarin: A Versatile Fullerene (C60) Receptor
Journal of the American Chemical Society ( IF 14.4 ) Pub Date : 2017-03-24 , DOI: 10.1021/jacs.7b00735
Xian-Sheng Ke ₁ , Taeyeon Kim ₂ , James T. Brewster ₁ , Vincent M. Lynch ₁ , Dongho Kim ₂ , Jonathan L. Sessler ₁

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An expanded rosarian (P3P6) with a bowl-like conformation has been prepared and characterized in a one-pot procedure that involves condensing a bispyrrole pyridine precursor (P1P2) with benzaldehyde, followed by oxidation. Single crystal X-ray diffraction analysis reveals a bowl-like conformation in the solid state with an upper rim diameter defined by the meso-phenyl substituents of ca. 13.5 Å and a depth of roughly 6.3 Å. P3P6 forms both 1:1 and 2:1 complexes with C60 in the solid state. DFT reveals similar energies for the two binding modes. A 1:1 binding stoichiometry dominates in 1,2-dichlorobenzene-d4 at the millimolar concentrations dictated by solubility consideration. The solution phase interactions between rosarian and C60 were studied using 1H NMR, UV-vis, and femtosecond transient absorption spectroscopies in 1,2-dichlorobenzene-d4 or toluene. To our knowledge, this is the first report of an unfunctionalized porphyrinoid that forms a well-defined complex with C60 in solution as well as in solid state.

中文翻译：

扩展的 Rosarin：多功能富勒烯 (C60) 受体

已经制备了具有碗状构象的膨胀玫瑰红 (P3P6) 并在一锅法中表征，该程序涉及将双吡咯吡啶前体 (P1P2) 与苯甲醛缩合，然后进行氧化。单晶 X 射线衍射分析揭示了固态下的碗状构象，其上边缘直径由约 10 的中间苯基取代基定义。13.5 Å，深度约为 6.3 Å。P3P6 在固态下与 C60 形成 1:1 和 2:1 复合物。DFT 揭示了两种结合模式的相似能量。1:1 结合化学计量在 1,2-二氯苯-d4 中以溶解度考虑所规定的毫摩尔浓度占主导地位。使用 1H NMR、UV-vis 和飞秒瞬态吸收光谱在 1、2-二氯苯-d4或甲苯。据我们所知，这是关于未官能化的卟啉类化合物的第一份报告，它与 C60 在溶液和固态中形成明确的复合物。

更新日期：2017-03-24

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