Intriguing electrochemical behavior of free base porphyrins: Effect of porphyrin- meso -phenyl interaction controlled by position of substituents on meso -phenyls

Tu Y.-J.; Cheng H.C.; Chao I.; Cho C.-R.; Cheng R.-J.; Su Y.O.

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Intriguing electrochemical behavior of free base porphyrins: Effect of porphyrin- meso -phenyl interaction controlled by position of substituents on meso -phenyls

机译：有趣的游离碱卟啉的电化学行为：卟啉-内消旋-苯基相互作用的影响受内消旋-苯基上取代基位置的控制

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Electrochemical properties of substituted free base meso- tetraphenylporphyrins (H _2T(o,o′-X)PP, H _2T(o-X)PP, and H _2T(p-X)PP, where X = OCH _3, CH _3, H, F, or Cl on the phenyl rings) are examined by cyclic voltammetry. When a substituent is located only at the para position of the meso-phenyl group, the difference between the first and second oxidation potentials (ΔE ~(ox), i.e., E _2 ~(ox) - E _1 ~(ox)), is generally significantly smaller than those of the H _2TPPs with bulky o,o′-substituents on the phenyl group. This trend is elucidated with density functional theory calculations and attributed mainly to the sterically controlled π-conjugation of the meso-phenyl groups to the central porphyrin ring, rather than the often discussed deformation of porphyrin.

机译：取代的游离碱中四苯基卟啉（H _2T（o，o'-X）PP，H _2T（oX）PP和H _2T（pX）PP的电化学性质，其中X = OCH _3，CH _3，H，F，或苯环上的Cl）通过循环伏安法检查。当取代基仅位于内苯基的对位时，第一和第二氧化电位之差（ΔE〜（ox），即E _2〜（ox）-E _1〜（ox）），通常比在苯基上具有大的o，o′-取代基的H _2TPP显着小。这种趋势已通过密度泛函理论计算得以阐明，并且主要归因于内苯基基团与中心卟啉环的空间控制π结合，而不是经常讨论的卟啉变形。

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《The journal of physical chemistry, A. Molecules, spectroscopy, kinetics, environment, & general theory》 |2012年第6期|共6页
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Tu Y.-J.; Cheng H.C.; Chao I.; Cho C.-R.; Cheng R.-J.; Su Y.O.;
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1. Intriguing electrochemical behavior of free base porphyrins: Effect of porphyrin- meso -phenyl interaction controlled by position of substituents on meso -phenyls [J] . Tu Y.-J., Cheng H.C., Chao I., The journal of physical chemistry, A. Molecules, spectroscopy, kinetics, environment, & general theory . 2012,第6期

机译：有趣的游离碱卟啉的电化学行为：卟啉-内消旋-苯基相互作用的影响受内消旋-苯基上取代基位置的控制
2. Direct Animation of meso-Tetraarylporphyrin Derivatives - Easy Route to A3B-, A2BC-, and A2B2-Type Porphyrins Bearing Two Nitrogen-Containing Substituents at the meso-Positioned Phenyl Groups [J] . Stanislaw Ostrowski, Sebastian Grzyb, Agnieszka Mikus Helvetica chimica acta . 2007,第10期

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Intriguing electrochemical behavior of free base porphyrins: Effect of porphyrin- meso -phenyl interaction controlled by position of substituents on meso -phenyls

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