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Synthesis, Structure, Photophysical Properties, and Photostability of Benzodipyrenes
Wenlong Yang1, Jorge H S K Monteiro1, Ana de Bettencourt-Dias1
1Department of Chemistry, University of Nevada, Reno, 1664 N. Virginia St., Reno, NV, 89557, USA.
Abstract:
This work explores the syntheses, structures, photophysical properties, and photostability of benzodipyrenes (BDPs). BDPs were synthesized through an InCl3 -AgNTf2 -catalyzed, four-fold alkyne benzannulation reaction. The structures of BDP 4 a and its corresponding endoperoxide product were unambiguously confirmed by X-ray crystallography. The BDPs reported here can also be recognized as peri- and cata-benzannulated pentacenes with a non-functionalized central ring. Unlike the previous reported pentacene-based polycyclic aromatic hydrocarbons, the absorbances of the BDPs were blueshifted by ca. 40 nm relative to pentacene, even after extension of π-conjugation. The newly synthesized BDP products exhibit relatively good stability with half-lives as high as 4612 min in THF.
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