Organic Letters
Organic Letters
5 years ago

Synthesis and Properties of Conjugated Macrocycles Containing 2,7-Bis(2-thienyl)-9H-fluoren-9-one Units

Synthesis and Properties of Conjugated Macrocycles Containing 2,7-Bis(2-thienyl)-9H-fluoren-9-one Units
Brian V. Popp, Haresh Thakellapalli, Notashia N. Baughman, Novruz G. Akhmedov, Kung K. Wang, Behzad Farajidizaji, Shuangjiang Li
Synthetic pathways to conjugated macrocycles containing one, two, or three 2,7-bis(2-thienyl)-9H-fluoren-9-one (TFOT) units in the macrocyclic frameworks bearing 10, 16, or 24 aromatic units were developed. The Diels–Alder reaction between (E,E)-1-(5-bromo-2-thienyl)-4-(5-iodo-2-thienyl)-1,3-butadiene and dimethyl acetylenedicarboxylate produced the key Diels–Alder adduct for the subsequent macrocyclic ring formation. UV–vis and fluorescence spectra of the TFOT-containing molecules were recorded, and their electrochemical properties were investigated by cyclic and differential pulse voltammetry. Solvatofluorochromic properties were observed for the TFOT-containing molecules.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b01019

DOI: 10.1021/acs.orglett.7b01019

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