Dimerization of a Reactive Azaacene Diradical: Synthesis of a Covalent Azaacene Cage.
Angew Chem Int Ed Engl
; 62(32): e202305712, 2023 Aug 07.
Article
em En
| MEDLINE
| ID: mdl-37219544
ABSTRACT
Two series of regioisomeric dicyanomethylene substituted dithienodiazatetracenes with formal para- or ortho-quinodimethane subunits were synthesized and characterized. Whereas the para-isomers (p-n, diradical index y0 =0.01) are stable and isolable, the ortho-isomer (y0 =0.98) dimerizes into a covalent azaacene cage. Four elongated σ-CC bonds are formed and the former triisopropylsilyl(TIPS) -ethynylene groups transformed into cumulene units. The azaacene cage dimer (o-1)2 was characterized by X-ray single crystal structure analysis and temperature-dependent infrared (IR), electron paramagnetic resonance (EPR, solid-state), nuclear magnetic resonance (NMR) and ultraviolet-visible (UV/Vis) spectroscopies (solution) indicating reformation of o-1.
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MEDLINE
Idioma:
En
Ano de publicação:
2023
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Article