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

Bradley D. Rose; Peter J. Santa Maria; Aaron G. Fix; Chris L. Vonnegut; Lev N. Zakharov; Sean R. Parkin; Michael M. Haley

doi:10.3762/bjoc.10.219

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

Bradley D. Rose, Peter J. Santa Maria, Aaron G. Fix, Chris L. Vonnegut, Lev N. Zakharov, Sean R. Parkin, Michael M. Haley

Chemistry

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

17 Scopus citations

Abstract

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.

Original language	English
Pages (from-to)	2122-2130
Number of pages	9
Journal	Beilstein Journal of Organic Chemistry
Volume	10
DOIs	https://doi.org/10.3762/bjoc.10.219
State	Published - Sep 5 2014

Bibliographical note

Publisher Copyright:
© 2014 Rose et al; licensee Beilstein-Institut.

Funding

Funders	Funder number
National Stroke Foundation	DGE-0742540
National Science Foundation (NSF)	1062512

Keywords

Crystal packing
Electron accepting
Indenofluorenes
Organic electronics
Polycyclic conjugated hydrocarbons

ASJC Scopus subject areas

Organic Chemistry

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10.3762/bjoc.10.219

Cite this

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

abstract = "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.",

keywords = "Crystal packing, Electron accepting, Indenofluorenes, Organic electronics, Polycyclic conjugated hydrocarbons",

author = "Rose, {Bradley D.} and {Santa Maria}, {Peter J.} and Fix, {Aaron G.} and Vonnegut, {Chris L.} and Zakharov, {Lev N.} and Parkin, {Sean R.} and Haley, {Michael M.}",

note = "Publisher Copyright: {\textcopyright} 2014 Rose et al; licensee Beilstein-Institut.",

year = "2014",

month = sep,

day = "5",

doi = "10.3762/bjoc.10.219",

language = "English",

volume = "10",

pages = "2122--2130",

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T1 - Scalable synthesis of 5,11-diethynylated indeno[1,2-b]fluorene-6,12-diones and exploration of their solid state packing

AU - Rose, Bradley D.

AU - Santa Maria, Peter J.

AU - Fix, Aaron G.

AU - Vonnegut, Chris L.

AU - Zakharov, Lev N.

AU - Parkin, Sean R.

AU - Haley, Michael M.

PY - 2014/9/5

Y1 - 2014/9/5

N2 - 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.

AB - 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.

KW - Crystal packing

KW - Electron accepting

KW - Indenofluorenes

KW - Organic electronics

KW - Polycyclic conjugated hydrocarbons

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JO - Beilstein Journal of Organic Chemistry

JF - Beilstein Journal of Organic Chemistry

ER -

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

Abstract

Bibliographical note

Funding

Keywords

ASJC Scopus subject areas

Access to Document

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