Syntheses and Properties of Nonplanar Circulene Featuring a Structural Motif in Carbon Cluster

碳团簇结构基序非平面圆烯的合成与性能

• 批准号: 05453036
• 负责人: YAMAMOTO Koji
• 金额: $ 3.78万
• 依托单位: University of Osaka Prefecture
• 依托单位国家: 日本
• 项目类别: Grant-in-Aid for General Scientific Research (B)
• 财政年份: 1993
• 资助国家: 日本
• 起止时间: 1993 至 1995
• 项目状态: 已结题
• 来源: https://kaken.nii.ac.jp/en/grant/KAKENHI-PROJECT-05453036/
• 关键词: Condensed Aromatic Compound; Strained Molecule; Nonplanar Molecule; Cluster; Circulene; フラーレン

Recent advances in large carbon cluster chemistry (fullerenes) with curved molecular surfaces on sp^2 carbon lattices have aroused a interest in the field of nonplanar polycyclic aromatic compounds with circular arrangement of benzene rings known as circulene. The nonplanar circulenes featuring a structural motif present in carbon clusters were prepared and their unusual physical and chemical properties resulting from their stained and nonplanar structure were reported.1. Convenient new synthesis of [7] Circulene [7] Circulene with saddle-shaped geometry was prepared by a convenient new method via 2,15-ethanobridged hexahelicene intermediate and its electrochemical properties was also examined.2. Synthesis and characterization of hepta [5][5] circulene The polycyclic aromatic compound with a S-shaped circular arrangement of seven benzene rings, hepta [5][5] circulene, was prepared by FVP of bis- (1-chlorovinyl) acenaphthofluorancene. The structure and electrochemical properties were examined.3. Ring inversion of [7] circulene derivative Our recent development of a convenient new route to [7] circulene and derivatives ther of has enabled us to measure the saddle-to-saddle inversion barrier for twisted saddle-shaped network at trigonal carbon atoms from variable temperature NMR experiments.4. Synthesis of [7][7] circulene The preparation of [7][7] circulene whose carbon framework represents a subunit of helix-shaped nanotube inner surface was reported.

在sp^2碳晶格上具有弯曲分子表面的大碳团簇化学（富勒烯）的最新进展引起了人们对苯环呈圆形排列的非平面多环芳香族化合物（称为环烯）的兴趣。制备了以碳簇中存在的结构基序为特征的非平面环烯，并对其染色和非平面结构所导致的异常物理和化学性质进行了表征. [7]环烯的简便新合成方法[7]通过2，15-乙撑桥六螺烯中间体，采用简便的新方法合成了具有鞍形几何构型的环烯，并对其电化学性质进行了研究.七[5][5]环烯的合成与表征以双（1-氯乙烯基）苊并荧蒽为原料，通过FVP反应合成了七个苯环的S形环状芳香族化合物七[5][5]环烯。并对其结构和电化学性能进行了研究. [7]环烯衍生物的环反转我们最近开发了一种方便的合成[7]环烯及其衍生物的新方法，使我们能够从变温NMR实验中测量三角碳原子上扭曲鞍形网络的鞍到鞍反转势垒. [7][7]环烯的合成报道了以螺旋状纳米管内表面的亚基为碳骨架的[7][7]环烯的制备。

项目成果

Koji Yamamoto: "Novel Optically Active 7,7'-Bridged-1,1'-biiso- quinol ines and Their Cheration to Rhodium (I) lon" J.Chem.Soc.,Chem.Commun.1637-1638 (1995)

Koji Yamamoto：“新型光学活性 7,7-桥接-1,1-二异喹啉及其对铑 (I) lon 的螯合”J.Chem.Soc.,Chem.Commun.1637-1638 (1995)

Hiroyuki Higuchi, Kaoru Asano, Juro Ojima, Koji Yamamoto, Toshikatsu Yoshida, Tomohiro Adachi, Gaku Yamamoto: "Synthesis and Properties of Methano-bridged Dichlorodidehydro [16]-, [20]-, [24] annulenediones" J.Chem.Soc., Perkin Trans.1. 67. 778-791 (1994)

Hiroyuki Higuchi、Kaoru Asano、Juro Ojima、Koji Yamamoto、Toshikatsu Yoshida、Tomohiro Adachi、Gaku Yamamoto：“甲醇桥联二氯二氢 [16]-、[20]-、[24] 环烯二酮的合成和性质”J.Chem.Soc

Masanori Matsuda, Hiroshi Matsubara, Susumu Okamoto, Koji Yamamoto: "Synthesis and Characterization of Hepta- [5][5] circulene as Subunit of C_<70> Fullerene" Chem.Lett. 157-158 (1996)

Masanori Matsuda、Hiroshi Matsubara、Susumu Okamoto、Koji Yamamoto：“作为 C_<70> 富勒烯亚基的 Hepta-[5][5] circulene 的合成和表征”Chem.Lett。

Masahiko Iyoda: "Synthesis and Properties of a Bisdehydro[14]annuleno[c]furan and an Ortho-Annelated Tetrakisdehydro[14]annulene" Bull.Chem.Soc.Jpn.(in press). (1994)

Masahiko Iyoda：“双脱氢[14]环烯[c]呋喃和邻位环环四脱氢[14]环烯的合成和性质”Bull.Chem.Soc.Jpn.（出版中）。

Hiroyuki Higuchi: "Synthesis and Properties of Methano-Bridged Dichlorodidehydro-[16]-,-[20]-,and-[24]-annulenones" J.Chem.Soc.,Perkin Trans.I. (in press). (1994)

Hiroyuki Higuchi：“甲醇桥联二氯二氢-[16]-、-[20]-和-[24]-轮环酮的合成和性质”J.Chem.Soc.，Perkin Trans.I。