Abstract
We describe the synthesis and electronic properties of the novel interrupted hexacene 5,16-diphenylcyclobuta[1,2-b:3,4-b′]dianthracene (1). The synthesis is rooted in a sequential twin Sonogashira coupling of 2,3-dibromo-9,10-dihydro-9,10-epoxyanthracene followed by a Vollhardt 2+2+2 cyclotrimerization to give o-bromoaryl(trimethylsilyl) 8, after selective bromination. A Diels-Alder cycloaddition of the aryne from 8 and 1,3-diphenylisobenzofuran gave 1 after deoxygenation. Photophysical studies suggest that the fused cyclobutane ring been the two anthracene rings allows through-conjugation, but does not allow 1 to behave as a conjugated acene. Attempts to synthesize the parent analogue, cyclobuta[1,2-b:3,4-b′]dianthracene (2) were not successful, but detailed calculations are reported for both 1 and 2.
Original language | English |
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Article number | 152182 |
Journal | Tetrahedron Letters |
Volume | 61 |
Issue number | 31 |
DOIs | |
State | Published - Jul 30 2020 |
Bibliographical note
Funding Information:GWG acknowledges support by the donors of the Petroleum Research Fund administered by the American Chemical Society. PZM thanks Dartmouth College for a Zabriskie Fellowship.
Funding Information:
GWG acknowledges support by the donors of the Petroleum Research Fund administered by the American Chemical Society . PZM thanks Dartmouth College for a Zabriskie Fellowship.
Publisher Copyright:
© 2020 Elsevier Ltd
Copyright:
Copyright 2020 Elsevier B.V., All rights reserved.
Keywords
- Anthracene
- DFT calculations
- Diels-Alder cycloaddition
- Fused cyclobutanes
- Photophysical studies
- Polycyclic aromatic hydrocarbons
- UV/Vis absorption
ASJC Scopus subject areas
- Biochemistry
- Drug Discovery
- Organic Chemistry