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

Research output: Contribution to journalArticlepeer-review

18 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 languageEnglish
Pages (from-to)2122-2130
Number of pages9
JournalBeilstein Journal of Organic Chemistry
Volume10
DOIs
StatePublished - Sep 5 2014

Bibliographical note

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

Funding

FundersFunder number
National Stroke FoundationDGE-0742540
National Stroke Foundation
U.S. Department of Energy Chinese Academy of Sciences Guangzhou Municipal Science and Technology Project Oak Ridge National Laboratory Extreme Science and Engineering Discovery Environment National Science Foundation National Energy Research Scientific Computing Center National Natural Science Foundation of China1062512, 0742540, 1013032
U.S. Department of Energy Chinese Academy of Sciences Guangzhou Municipal Science and Technology Project Oak Ridge National Laboratory Extreme Science and Engineering Discovery Environment National Science Foundation National Energy Research Scientific Computing Center National Natural Science Foundation of China

    Keywords

    • Crystal packing
    • Electron accepting
    • Indenofluorenes
    • Organic electronics
    • Polycyclic conjugated hydrocarbons

    ASJC Scopus subject areas

    • Organic Chemistry

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