Covalent dimers of 1,3-diphenylisobenzofuran for singlet fission: synthesis and electrochemistry.
The synthesis of covalent dimers in which two 1,3-diphenylisobenzofuran units are connected through one phenyl substituent on each is reported. In three of the dimers, the subunits are linked directly, and in three others, they are linked via an alkane chain. A seventh new compound in which two 1,3-diphenylisobenzofuran units share a phenyl substituent is also described. These materials are needed for investigations of the singlet fission process, which promises to increase the efficiency of solar cells. The electrochemical oxidation and reduction of the monomer, two previously known dimers, and the seven new compounds have been examined, and reversible redox potentials have been compared with results obtained from density functional theory. Although the overall agreement is satisfactory, some discrepancies are noted and discussed.
†Department of Chemistry and Biochemistry, University of Colorado, Boulder, Colorado 80309-0215, United States.|‡Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, 16610 Prague 6, Czech Republic.
Akin
A
Akdag
§J. Heyrovský Institute of Physical Chemistry, Academy of Sciences of the Czech Republic, Dolejškova 3, 18223 Prague 8, Czech Republic.
Abdul
A
Wahab
‡Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, 16610 Prague 6, Czech Republic.
Pavel
P
Beran
‡Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, 16610 Prague 6, Czech Republic.
Lubomír
L
Rulíšek
†Department of Chemistry and Biochemistry, University of Colorado, Boulder, Colorado 80309-0215, United States.
Paul I
PI
Dron
§J. Heyrovský Institute of Physical Chemistry, Academy of Sciences of the Czech Republic, Dolejškova 3, 18223 Prague 8, Czech Republic.
Jiří
J
Ludvík
†Department of Chemistry and Biochemistry, University of Colorado, Boulder, Colorado 80309-0215, United States.|‡Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, 16610 Prague 6, Czech Republic.
Josef
J
Michl