Successful incorporation of singlet fission (SF) into modern optoelectronic architectures depends upon precise control over intermolecular orientations of SF chromophores. This task is complicated by the need to fulfill at least two criteria, fast SF and efficient interfacial energy or charge transfer to an acceptor. For dye sensitized solar cells or ligand exchanged quantum dots, SF chromophores are chemically tethered to the semiconductor through solution phase surface-binding reactions which represents a unique opportunity to synthetically tune the chromophore orientation and distance from the surface. The nature of the chromophore’s behavior in the concentrated solutions necessary for surface binding is seldom investigated or considered even though it has a direct impact on the uniformity and availability for surface coverage. In this study, we characterize the solution phase behavior of a new mono-carboxylated tetracene derivative, TIPS COOH Tc, in the context of its photophysics for solar light harvesting and surface chemistry at a nanoscale interface. Through <sup>1</sup>H-NMR, steady state and time resolved spectroscopy, we find that TIPS COOH Tc can either be monomeric or in an aggregated state that displays excimeric signatures. The behavior can be traced to the solvent polarity, solvent hydrogen bond character, and TIPS COOH Tc concentration. These insights are then applied to ligand exchange with oleate capped PbS quantum dots where choice of solvent impacts the amount of surface coverage as well as the likely binding and aggregation motifs.

Unraveling hydrogen bond aggregation of a mono-carboxylated tetracene derivative

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ACS Fall 2022

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