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Photoacoustic imaging (PAI) relies on the use of contrast agents with high molar absorptivity in the NIR-I/NIR-II region. Expanded porphyrins, synthetic analogues of natural tetrapyrrolic pigments ( e.g.  heme and chlorophyll), constitute as potentially attractive platforms due to their NIR-II absorptivity and their ability to respond to stimuli. Here, we evaluate two expanded porphyrins, naphthorosarin ( 1 ) and octaphyrin ( 4 ), as stimuli responsive PA contrast agents for functional PAI. Both undergo proton-coupled electron transfer to produce species that absorb well in the NIR-II region. Octaphyrin ( 4 ) was successfully encapsulated into 1,2-distearoyl- sn -glycero-3-phosphoethanolamine-poly(ethylene glycol) (DSPE-PEG 2000 ) nanoparticles to afford  OctaNPs . In combination with PAI,  OctaNPs  allowed changes in the acidic environment of the stomach to be visualized and cancerous  versus  healthy tissues to be discriminated.

Expanded porphyrins: functional photoacoustic imaging agents that operate in the NIR-II region