Small-Molecule Porphyrin-Based Organic Nanoparticles with Remarkable Photothermal Conversion Efficiency for in Vivo Photoacoustic Imaging and Photothermal Therapy.

Near-infrared (NIR)-absorbing organic nanoparticles (ONPs) are emerging candidates for "one-for-all" theranostic nanomaterials with considerations of safety and formulation in mind. However, facile fabrication methods and improvements in the photothermal conversion efficiency (PCE) and photostability are likely needed before a clinically viable set of candidates emerges. Herein, a new organic compound, [porphyrin-diketopyrrolopyrrole (Por-DPP)] with the donor-acceptor structure was synthesized, where porphyrin was used as a donor unit while diketopyrrolopyrrole was used as an acceptor unit. Por-DPP exhibited efficient absorption extending from visible to NIR regions. After self-assembling into nanoparticles (NPs) (∼120 nm), the absorption spectrum of Por-DPP NPs broadened and red-shifted to some extent, relative to that of organic molecules. Furthermore, the architecture of NPs enhanced the acceptor-donor structure, leading to emission quenching and facilitating nonradiative thermal generation. The PCE of Por-DPP NPs was measured and calculated to be 62.5%, higher than most of ONPs. Under 808 nm laser irradiation, the Por-DPP NPs possessed a distinct photothermal therapy (PTT) effect in vitro and can damage cancer cells efficiently in vivo without significant side effects after phototherapy. Thus, the small-molecule porphyrin-based ONPs with high PCE demonstrated promising application in photoacoustic imaging-guided PTT.