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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

Haresh Thakellapalli, Shuangjiang Li, Behzad Farajidizaji, Notashia N Baughman, Novruz G Akhmedov, Brian V Popp, Kung K Wang

Org Lett. 2017 May 19;19(10):2674-2677.

PMID: 28492330

Abstract:

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.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP1393528998	4,7-Bis(5-bromo-2-thienyl)-5,6-difluoro-2-octyl-2H-benzotriazole		1393528-99-8	Price

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