Synthesis and properties of polycyclic quinones condensed with 1,6-methano[10]annulene

Shigeyasu Kuroda; Mitsunori Oda; Hiroaki Takamatsu; Hirofumi Hatakeyama; Chisa Noda; Yanmei Zhang; Ryuta Miyatake; Nguyen Chung Thanh; Atsusi Yanagida; Mayumi Kyougoku; Takanori Kawakami

doi:10.1016/j.stam.2007.01.009

Synthesis and properties of polycyclic quinones condensed with 1,6-methano[10]annulene

Shigeyasu Kuroda^*, Mitsunori Oda, Hiroaki Takamatsu, Hirofumi Hatakeyama, Chisa Noda, Yanmei Zhang, Ryuta Miyatake, Nguyen Chung Thanh, Atsusi Yanagida, Mayumi Kyougoku, Takanori Kawakami

^*Corresponding author for this work

Center for Environmental Conservation and Research Safety

Research output: Contribution to journal › Article › peer-review

6 Scopus citations

Abstract

Two types of polycyclic quinones condensed with 1,6-methano[10]annulenes as type A: 1,6-methanonaphtho[2,3-c][10]annulene-7,12-dione 5a, and type B: 1,6-methanonaphtho[2,3-c][10]annulene-5,14-dione 18, bis(1,6-methano[10]annuleno[3,4-b; 3,4-g])anthracene-10,21-dione 20, 1,6-methanoanthraceno[2,3-c][10]annulene-5,16-dione 22, 1,6-methanotetraceno[2,3-c][10]annulene-6,17-dione 23, and 1,6-methano phenanthreno[2,3-c][10]annulene-5,6-dione 24 have been synthesized. The acene derivative 6 corresponding to that of 5a was synthesized by the reduction of quinone 5a. The physical, spectral, and chemical properties of these new compounds have been investigated.

Original language	English
Pages (from-to)	306-317
Number of pages	12
Journal	Science and Technology of Advanced Materials
Volume	8
Issue number	4
DOIs	https://doi.org/10.1016/j.stam.2007.01.009
State	Published - 2007/05

Keywords

Bridged [10]annulene
Condensed acene
Fluorescence
Poly condensed quinone
Rearrangement
Reduction potentials

ASJC Scopus subject areas

General Materials Science

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10.1016/j.stam.2007.01.009

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@article{50a061b9e9f24ca69a51065e13fbe932,

title = "Synthesis and properties of polycyclic quinones condensed with 1,6-methano[10]annulene",

abstract = "Two types of polycyclic quinones condensed with 1,6-methano[10]annulenes as type A: 1,6-methanonaphtho[2,3-c][10]annulene-7,12-dione 5a, and type B: 1,6-methanonaphtho[2,3-c][10]annulene-5,14-dione 18, bis(1,6-methano[10]annuleno[3,4-b; 3,4-g])anthracene-10,21-dione 20, 1,6-methanoanthraceno[2,3-c][10]annulene-5,16-dione 22, 1,6-methanotetraceno[2,3-c][10]annulene-6,17-dione 23, and 1,6-methano phenanthreno[2,3-c][10]annulene-5,6-dione 24 have been synthesized. The acene derivative 6 corresponding to that of 5a was synthesized by the reduction of quinone 5a. The physical, spectral, and chemical properties of these new compounds have been investigated.",

keywords = "Bridged [10]annulene, Condensed acene, Fluorescence, Poly condensed quinone, Rearrangement, Reduction potentials",

author = "Shigeyasu Kuroda and Mitsunori Oda and Hiroaki Takamatsu and Hirofumi Hatakeyama and Chisa Noda and Yanmei Zhang and Ryuta Miyatake and Thanh, {Nguyen Chung} and Atsusi Yanagida and Mayumi Kyougoku and Takanori Kawakami",

year = "2007",

month = may,

doi = "10.1016/j.stam.2007.01.009",

language = "英語",

volume = "8",

pages = "306--317",

journal = "Science and Technology of Advanced Materials",

issn = "1468-6996",

publisher = "Taylor and Francis Ltd.",

number = "4",

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TY - JOUR

T1 - Synthesis and properties of polycyclic quinones condensed with 1,6-methano[10]annulene

AU - Kuroda, Shigeyasu

AU - Oda, Mitsunori

AU - Takamatsu, Hiroaki

AU - Hatakeyama, Hirofumi

AU - Noda, Chisa

AU - Zhang, Yanmei

AU - Miyatake, Ryuta

AU - Thanh, Nguyen Chung

AU - Yanagida, Atsusi

AU - Kyougoku, Mayumi

AU - Kawakami, Takanori

PY - 2007/5

Y1 - 2007/5

N2 - Two types of polycyclic quinones condensed with 1,6-methano[10]annulenes as type A: 1,6-methanonaphtho[2,3-c][10]annulene-7,12-dione 5a, and type B: 1,6-methanonaphtho[2,3-c][10]annulene-5,14-dione 18, bis(1,6-methano[10]annuleno[3,4-b; 3,4-g])anthracene-10,21-dione 20, 1,6-methanoanthraceno[2,3-c][10]annulene-5,16-dione 22, 1,6-methanotetraceno[2,3-c][10]annulene-6,17-dione 23, and 1,6-methano phenanthreno[2,3-c][10]annulene-5,6-dione 24 have been synthesized. The acene derivative 6 corresponding to that of 5a was synthesized by the reduction of quinone 5a. The physical, spectral, and chemical properties of these new compounds have been investigated.

AB - Two types of polycyclic quinones condensed with 1,6-methano[10]annulenes as type A: 1,6-methanonaphtho[2,3-c][10]annulene-7,12-dione 5a, and type B: 1,6-methanonaphtho[2,3-c][10]annulene-5,14-dione 18, bis(1,6-methano[10]annuleno[3,4-b; 3,4-g])anthracene-10,21-dione 20, 1,6-methanoanthraceno[2,3-c][10]annulene-5,16-dione 22, 1,6-methanotetraceno[2,3-c][10]annulene-6,17-dione 23, and 1,6-methano phenanthreno[2,3-c][10]annulene-5,6-dione 24 have been synthesized. The acene derivative 6 corresponding to that of 5a was synthesized by the reduction of quinone 5a. The physical, spectral, and chemical properties of these new compounds have been investigated.

KW - Bridged [10]annulene

KW - Condensed acene

KW - Fluorescence

KW - Poly condensed quinone

KW - Rearrangement

KW - Reduction potentials

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JO - Science and Technology of Advanced Materials

JF - Science and Technology of Advanced Materials

IS - 4

ER -

Synthesis and properties of polycyclic quinones condensed with 1,6-methano[10]annulene

Abstract

Keywords

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