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

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

Volume: 12 Issue: 5

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

Affiliation:

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

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 λ_onset of 366 nm (E_g = 3.4 eV), but the more highly conjugated 2,6-bis(9’-anthracylethynyl)anthraquinones exhibited a λ_onset of approximately 540 nm (E_g = 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.

Cite this article as:

Tumuluri Anusha, Khanna Bhanupriya, Altalib Ammar and Revell D. Kevin, Synthesis and Electro-Optical Evaluation of 2,6-Bis(arylethynyl)anthraquinones, Letters in Organic Chemistry 2015; 12 (5) . https://dx.doi.org/10.2174/1570178612666150203004458