Scalable synthesis of 5,11-diethynylated indeno[1,2-b]fluorene-6,12-diones and exploration of their solid state packing

被引：16

作者：

Rose, Bradley D. ^{[1
,2
]}

Maria, Peter J. Santa ^{[1
,2
]}

Fix, Aaron G. ^{[1
,2
]}

Vonnegut, Chris L. ^{[1
,2
]}

Zakharov, Lev N. ^{[3
]}

Parkin, Sean R. ^{[4
]}

Haley, Michael M. ^{[1
,2
]}

机构：

[1] Univ Oregon, Dept Chem & Biochem, Eugene, OR 97403 USA

[2] Univ Oregon, Inst Mat Sci, Eugene, OR 97403 USA

[3] Univ Oregon, CAMCOR, Eugene, OR 97403 USA

[4] Univ Kentucky, Dept Chem, Lexington, KY 40506 USA

来源：

BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY | 2014年 / 10卷

基金：

美国国家科学基金会;

关键词：

crystal packing; electron accepting; indenofluorenes; organic electronics; polycyclic conjugated hydrocarbons; CRYSTAL-STRUCTURES; ELECTRON; TRANSPORT;

D O I：

10.3762/bjoc.10.219

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We report a new synthetic route to 5,11-disubstituted indeno[1,2-b]fluorene-6,12-diones that is amenable to larger scale reactions, allowing for the preparation of gram amounts of material. With this new methodology, we explored the effects on crystal packing morphology for the indeno[1,2-b]fluorene-6,12-diones by varying the substituents on the silylethynyl groups.

引用

页码：2122 / 2130

页数：9

共 13 条

[1] Synthesis and crystal structures of alkynylated indeno[1,2-b]fluorene-6,12-diones
Santa Maria, Peter J.
Rose, Bradley D.
Haley, Michael M.
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2013, 245
[2] Synthesis and Optoelectronic Properties of Indeno[1,2-b]fluorene-6,12-dione Donor-Acceptor-Donor Triads
Frederickson, Conerd K.
Haley, Michael M.
JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (22): : 11241 - 11245
[3] Synthesis and Characterization of New Indeno[1,2-b]fluorene6,12-dione Derivatives
Wang Jing
Wu Linli
Wang Qian
CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2023, 43 (01) : 223 - 228
[4] Theoretical study of charge-transport and optical properties of indeno[1,2-b] fluorene-6,12-dione-based semiconducting materials
Huang, Jin-Dou
Zhao, Jinfeng
Yu, Kun
Huang, Xiaohua
Cheng, Shi-Bo
Ma, Huipeng
ACTA CRYSTALLOGRAPHICA SECTION B-STRUCTURAL SCIENCE CRYSTAL ENGINEERING AND MATERIALS, 2018, 74 : 705 - 711
[5] Boosting the Charge Transport Property of Indeno[1,2-b]fluorene-6,12-dione though Incorporation of Sulfur- or Nitrogen-Linked Side Chains
Fan, Zhi-Ping
Li, Xiang-Yang
Luo, Xiao-E.
Fei, Xian
Sun, Bing
Chen, Li-Chuan
Shi, Zi-Fa
Sun, Chun-Lin
Shao, Xiangfeng
Zhang, Hao-Li
ADVANCED FUNCTIONAL MATERIALS, 2017, 27 (45)
[6] Efficient, gram scale synthesis tof 5,11-substituted indeno[1,2-b]fluorenes
Stockwell, Chelsea E.
Chase, Daniel T.
Nobusue, Shunpei
Haley, Michael M.
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2011, 241
[7] Design, synthesis, and characterization of α,ω-disubstituted indeno[1,2-b]fluorene-6,12-dione-thiophene molecular semiconductors. Enhancement of ambipolar charge transport through synthetic tailoring of alkyl substituents
Ozdemir, Mehmet
Choi, Donghee
Kwon, Guhyun
Zorlu, Yunus
Kim, Hyekyoung
Kim, Myung-Gil
Seo, SungYong
Sen, Unal
Citir, Murat
Kim, Choongik
Usta, Hakan
RSC ADVANCES, 2016, 6 (01): : 212 - 226
[8] Synthesis of Benz[d]indeno[1,2-b]pyran-5,11-diones: Versatile intermediates for the design and synthesis of topoisomerase I inhibitors
Morrell, Andrew
Antony, Smitha
Kohlhagen, Glenda
Pommier, Yves
Cushman, Mark
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2006, 231
[9] Synthesis of benz[d]indeno[1,2-b]pyran-5,11-diones:: Versatile intermediates for the design and synthesis of topoisomerase I inhibitors
Morrell, A
Antony, S
Kohlhagen, G
Pommier, Y
Cushman, M
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2006, 16 (07) : 1846 - 1849
[10] SYNTHESES ON THE BASE OF DIMETHYLPYRAZOLES .9. SYNTHESIS AND SPECTRAL PROPERTIES OF ISOMERIC PYRAZOLO[3',4'-5,6] AND PYRAZOLO[5',4'-5,6]PYRIMIDO[1,2-B]-BENZO[D,E]ISOQUINOLINE-4,12-DIONES
PEREVALOV, VP
ANDREEVA, MA
BARYSHNENKOVA, LI
GURVICH, VY
STEPANOV, BI
KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 1990, (02): : 237 - 241

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