Shape-Selective Synthesis of Pentacene Macrocycles and the Effect of Geometry on Singlet Fission

18 September 2020, Version 1
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

Pentacene’s extraordinary photophysical and electronic properties are highly dependent on intermolecular, through-space interactions. Macrocyclic arrangements of chromophores have been shown to provide a high level of control over these interactions, but few examples exist for pentacene due to inherent synthetic challenges. In this work, zirconocene-mediated alkyne coupling was used as a dynamic covalent C-C bond forming reaction to synthesize two geometrically distinct, pentacene-containing macrocycles on a gram scale and in four or fewer steps. Both macrocycles undergo singlet fission in solution, with rates that differ by an order of magnitude while the rate of triplet recombination is approximately the same. This independent modulation of singlet and triplet decay rates is highly desirable for the design of efficient singlet fission materials. The dimeric macrocycle adopts a columnar packing motif in the solid state, with large void spaces between pentacene units of the crystal lattice.

Keywords

Pentacene
Macrocycles
Singlet Fission
Dynamic Covalent Chemistry (DCC)
Organic Materials

Supplementary materials

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2020 09 16 Pentacene Paper-Final
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2020 09 16 Pentacene Paper SI Final
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2020 09 16 Pentacene Paper SI Final
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Compound 1b
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Compound 8
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Compound S1
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