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A series of tetra donor substituted [2.2]paracyclophane-based two-photon absorption (TPA) fluorophores were synthesized in neutral and cationic forms. The imaging activity of overall set of fluorophores was studied by the two-photon induced fluorescence (TPIF) method in a range of solvents. We also measured a clear progression toward a longer photoluminescence lifetime with increasing solvent polarity (intrinsic photoluminescence lifetime, τ i : ∼2 ns in toluene → 12-16 ns in water). The paracyclophane fluorophores with this unique property can be utilized as an optical polarity probe for the biomolecular substrates. The combined measurement of the two-photon fluorescence microscopy (TPM) cell image and TPIF lifetime can give us a better understanding of the biological processes and local environments in the cells.

Polarity Probing Two-Photon Fluorophores Based on [2.2]Paracyclophane