Multifunctional photoresponsive organic molecule for electric field sensing and modulation

Abstract: Organic molecules with nonlinear optical behavior have advanced a wide range of fields spanning from integrated photonics to biological imaging. With advances in microscopy, an emerging application is multifunctional nonlinear organic imaging agents. Unlike conventional imaging probes which simply emit light through single or multi photon processes, multifunctional materials allow systems to be simultaneously imaged and controlled. In this work, we report a multifunctional molecular probe for modulating and reporting electric fields. The probe molecule consists of two distinct functional modules which are connected by a long alkyl chain. The electric field detector module relies on the two-photon (2p) imaging agent and photo-induced electron transfer (PeT) dye, TPE. Two-photon imaging agents have demonstrated less damage and larger penetration depths in cells and live tissue imaging. The electric field modulator module relies on the organic photoconductor, NAI. To reduce cross-talk and optimize absorption and emission wavelengths, the molecular structure is first studied using density functional theory modeling, and then the multi-functional molecular probe is synthesized. The photophysical, photoconductivity, and biotoxicity of the probe molecule are studied in a range of solvents and solid state, and the results agree with the theoretical predictions. Specifically, 2p excitation in a biocompatible solvent is demonstrated, the photoconductivity is rapid and reversible, and the material has low cytotoxicity. Additionally, the entire system is optically controlled, including signal read-out, and the two modules can be operated simultaneously or individually. This work sets the stage for modulation and detection of bioelectric fields in a range of cell and tissue types.