Four new TPP-based chromophores (1–4) peripherally functionalized with dendrons containing 2-fluorenyl groups were studied for their potential to serve in photodynamic therapy. Their linear and nonlinear optical properties were investigated. With significant TPA cross-sections at 790 nm, good singlet oxygen generation capabilities and relatively large intrinsic fluorescence, sensitizers such as 1 might become particularly appealing for theranostics.