Synthesis, Optical Properties, and Electronic Structures of Tetrakis(pentafluorophenyl)tetrathiaisophlorin Dioxide

Mishra Vijay Lakshmi; Furuyama Taniyuki; Kobayashi Nagao; Goto Kenta; Miyazaki Takaaki; Yang Jye-Shane; Shinmyozu Teruo

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Synthesis, Optical Properties, and Electronic Structures of Tetrakis(pentafluorophenyl)tetrathiaisophlorin Dioxide

机译：四（五氟苯基）四硫代异黄酮二氧化物的合成，光学性质和电子结构

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The synthesis, structure, optical and redox properties, and electronic structure of tetrakis(pentafluorophenyl)tetrathiaisophlorin dioxide (12) are reported. Oxidation of tetrakis(pentafluorophenyl) tetrathiaisophlorin (11) with dimethyldioxirane afforded the oxidized product, which was the tetrathiaisophlorin with two thiophene 1-oxide moieties (12). More significant nonplanarity and greater bond length alternation in 12 than those of 11 were observed by X-ray structural analysis. The absorption spectrum of 12 contains two bands at lambda=348 and 276 nm, with a weak tail that extends to lambda approximate to 650 nm. Analysis of the magnetic circular dichroism spectrum of 12, based on Michl's 4N-perimeter model and molecular orbital calculations, indicate that the broad band at lambda=348 nm appears to contain N-2 and P-2 bands, and 12 is classified as a 4n pi system, similar to 11. The nuclear-independent chemical shift values and H-1 NMR spectroscopy data indicate that 12 has more antiaromatic character than 11.

机译：报道了四（五氟苯基）四硫代异黄酮二氧化物（12）的合成，结构，光学和氧化还原性质以及电子结构。用二甲基二环氧乙烷氧化四（五氟苯基）四硫噻吩甲酸酯（11）得到氧化产物，其为具有两个噻吩1-氧化物部分的四硫噻吩甲酸酯（12）。通过X射线结构分析观察到，与11相比，在12中更显着的非平面性和更大的键长交替。 12的吸收光谱在λ= 348和276 nm处包含两个谱带，并延伸到λ的弱尾巴接近650 nm。根据Michl的4N-周长模型和分子轨道计算，对12的磁性圆二色性光谱的分析表明，λ= 348 nm处的宽带似乎包含N-2和P-2谱带，将12归类为4n pi系统，类似于11。独立于核的化学位移值和H-1 NMR光谱数据表明，12具有比11更强的抗芳香性。

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《Chemistry: A European journal》 |2016年第27期|共8页
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Mishra Vijay Lakshmi; Furuyama Taniyuki; Kobayashi Nagao; Goto Kenta; Miyazaki Takaaki; Yang Jye-Shane; Shinmyozu Teruo;
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absorption; heterocycles; isophlorins; porphyrinoids; synthesis design;

机译：吸收;杂环;叶绿素;卟啉类化合物;合成设计;

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Synthesis, Optical Properties, and Electronic Structures of Tetrakis(pentafluorophenyl)tetrathiaisophlorin Dioxide

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