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Subphthalocyanine–triangulene dyads: Property tuning for light‐harvesting device applications

ABSTRACT: Abstract Organic photovoltaics relies on the development of stable chromophores and redox‐active organic molecules with tailor‐made HOMO/LUMO energies. Here, we present the synthesis and properties of novel dyads composed of boron subphthalocyanine (SubPc) and triangulene units, connected either at the peripheral position of the subphthalocyanine or at the axial boron. The connectivity has strong implications for the absorption and fluorescence properties of the dyads, as well as their redox properties. While the SubPc unit has a bowl shape, triangulene is a planar structural unit that allows dyads to dimerize in the solid state on account of π‐stacking interactions as shown by X‐ray crystallography of one of the dyads. The electronic properties were also studied computationally by density functional theory methods. Excellent agreement between experimental and computed data were obtained, showing that our computational method is a strong tool in the rational design of optimum molecules to ultimately obtain finely tuned molecules for device applications. Novel subphthalocyanine–triangulene dyads were synthesized and investigated both experimentally and computationally for their optical and redox properties; these properties were found to depend strongly on the connectivity and spatial orientations of the two units. Experimentally determined redox potentials for the molecules were found to match excellently with calculated potentials, showing the strength of our computational method for tailoring molecules with specific electronic properties.

SUBMITTER: Rasmussen M

PROVIDER: S-EPMC9306930 | biostudies-literature |

REPOSITORIES: biostudies-literature

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