Synthesis and Electro-Optical Evaluation of 2,6-Bis(arylethynyl)anthraquinones

Author(s): Anusha Tumuluri, Bhanupriya Khanna, Ammar Altalib, Kevin D. Revell.

Journal Name:Letters in Organic Chemistry

Volume 12 , Issue 5 , 2015

Abstract:

A series of 2,6-bis(arylethynyl)anthraquinones was prepared via double Sonogashira coupling to 2,6-diiodoanthraquinone, and characterized with regard to their optical and electronic properties. Substitution with a derivatized phenylethynyl group produced a λonset of 366 nm (Eg = 3.4 eV), but the more highly conjugated 2,6-bis(9’-anthracylethynyl)anthraquinones exhibited a λonset of approximately 540 nm (Eg = 2.3 eV). Poor solubility in the unsubstituted 9’-anthracylethynyl system hampered complete characterization or purification, but the 10’-hexanoylanthrac-9’-ylethynyl analog exhibited significantly better solubility. The preparation of several other functionalized derivatives was also explored, and key synthetic findings are reported.

Keywords: Anthraquinone, sonogashira coupling, organic semiconductor, HOMO-LUMO gap.

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Article Details

VOLUME: 12
ISSUE: 5
Year: 2015
Page: [337 - 343]
Pages: 7
DOI: 10.2174/1570178612666150203004458
Price: $58

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