Balancing fluorescence and singlet oxygen formation in push–pull type near-infrared BODIPY photosensitizers

Abstract

Rational, computationally guided, molecular design affords push–pull BODIPY photosensitizers with balanced brightness and phototoxicity for image-guided photodynamic therapy.

Near-infrared light activated photosensitizer with specific imaging of lipid droplets enables two-photon excited photodynamic therapy

“…Boron-dipyrromethene (BODIPY) derivatives have attracted considerable attention with lots of reports in the 1PE-PDT system since their unique chemical and physical properties. [38][39][40][41] Several strategies have been developed to facilitate the clinical trials for BODIPY-based PSs. For example, heavy atoms (e.g.…”

Bis-borylated arylisoquinoline-derived dyes with a central aromatic core: towards efficient fluorescent singlet-oxygen photosensitizers

“…Such dyes/photosensitizers could be spatially located through their fluorescence and would at the same time lead to the generation of therapeutically active 1 O 2 , as for example, implied in photodynamic therapy (PDT) of tumorous tissues. [37][38][39] In the context of organoboron structures, 1 O 2photosensitizing BODIPY dyes often include heavy atoms (bromine, iodine) to promote the population of the excited triplet state, which in turn is implied in energy transfer to triplet oxygen. 38,40 Accordingly, high 1 O 2 formation quantum yields (Φ Δ ) are observed for these dyes (typically 0.8-0.9), but relatively low fluorescence quantum yields (Φ f ), typically smaller than 0.1, result.…”

Unravelling the major factors in photo-oxidative stability of anthradithiophene derivatives

“…Endoperoxide formation has been utilised in a positive manner in the areas of oxygen sensing materials, 17 and since the reaction is often thermally reversible 18 it can also be used as a delivery method for reactive oxygen species (ROS) in applications such as photodynamic therapy. 19…”

“…Endoperoxide formation has been utilised in a positive manner in the areas of oxygen sensing materials, 17 and since the reaction is often thermally reversible 18 it can also be used as a delivery method for reactive oxygen species (ROS) in applications such as photodynamic therapy. 19 Photo-oxidation and endoperoxide formation can occur through two main mechanisms, 20 demonstrated in Scheme 1. In both cases, the acene (or an additional photosensitiser) is excited by the absorption of incident light.…”