Synthesis and Investigation of a Symmetrical Bis(methoxycarbonyl)-Substituted Rubrene Derivative
A symmetrical rubrene derivative, 5,6-bis(4-(methoxycarbonyl)phenyl)-11,12-diphenyltetracene, was synthesized via the thermal dimerization of 1,1-diphenyl-3-[4-(methoxycarbonyl)phenyl]-3-chloroallene. The reaction proceeded with the low selectivity typical of the classical “rubrenic synthesis” under these conditions, affording the target tetracene and the bis(alkylidene)cyclobutene by-product in nearly equal yields of 25% each. The optical characteristics of this rubrene derivative were investigated, revealing bright orange fluorescence in a CHCl3 solution (λem = 565 nm, ΦF = 0.81, τ = 11.41 ns), which is strongly quenched in the solid state (ΦF = 0.01) due to aggregation.
Authors
- A. N. Aleksandrov
- Alexander S. Steparuk (ORCID: https://orcid.org/0000-0003-3235-4674)
- Gennady L. Rusinov (ORCID: https://orcid.org/0000-0001-8567-9435)
- A. R. Tameev (ORCID: https://orcid.org/0000-0001-8865-3361)
- Ildar R. Sayarov (ORCID: https://orcid.org/0009-0003-5634-9420)
- Roman A. Irgashev
Institutions
- Frumkin Institute of Physical Chemistry and Electrochemistry Russian Academy of Sciences (RU)
- Institute of Organic Synthesis (RU)
- Ural Branch of the Russian Academy of Sciences (RU)
Publication Details
- Journal
- Molbank
- Published
- 2026-01-06
- DOI
- https://doi.org/10.3390/m2122
- Citations
- 1
- Primary Topic
- Synthesis and Properties of Aromatic Compounds
- Type
- article
- Field-Weighted Citation Impact
- 22.95
Funders
- Ministry of Education and Science of the Russian Federation
- Russian Science Foundation
- Russian Academy of Sciences
- Postovsky Institute of Organic Synthesis