Orthogonally aligned cyclic BODIPY arrays with long-lived triplet excited states as efficient heavy-atom-free photosensitizers

Abstract

Cyclic BODIPY trimers showed strong exciton coupling in singlet excited states and long-lived triplet excited states, and generated both singlet oxygen and superoxide radicals under light irradiation, giving good reactive oxygen quantum yields and promising PDT results in vitro.

Controlled assembly of a bicyclic porphyrinoid and its 3-dimensional boron difluoride arrays

“…520 nm) irradiation. Here, 1,3-diphenylisobenzofuran (DPBF) and Rose Bengal (RB) were used as the singlet oxygen scavenger and reference compound, 33 respectively. A time-dependent decrease in the absorbance of DPBF ( λ max = 414 nm) was seen upon irradiation of the BODIPY arrays in CH 2 Cl 2 solution, whereas no detectable decrease was seen in the dark (Fig.…”

“…The strong exciton coupling 22,24 expected for systems containing more than one BODIPY-like subunit has made such systems of interest in the context of specic applications, including lightharvesting, uorescence-based sensor development, and photodynamic therapy (PDT). [27][28][29][30][31][32][33] Recently, Werz and co-workers prepared a series of benzene-fused oligo-BODIPYs containing up to 31 rings that exhibited intriguing NIRabsorbing and redox properties. 34 Early on several macrocyclic BODIPY arrays incorporating 1,4-and 1,3-phenylene moieties were reported by Nabeshima and co-workers, which were shown to act as hosts for cationic guests.…”

Boron-Templated Synthesis of B(III)-Submonoazaporphyrins: The Hybrids of B(III)-Subporphyrins and B(III)-Subporphyrazines

“…Inspired by our recent success of building boron-functionalized BODIPYs from arylboronic acids, we chose the key precursor, α-amino-α′-bromotripyrromethene, since we rationalized that it may coordinate with arylboronic acid to form a boron complexed tripyrrolic intermediate, which then undergoes an intramolecular nucleophilic substitution to possibly obtain a new subporphyrin hybrid (Figure b). Thus, α-amino-α′-bromotripyrromethene 1a was first reacted with equal amount of phenylboronic acid in the presence of Na 2 CO 3 in refluxing toluene (Scheme a), from which only one major product was gradually generated.…”

Core–shell magnetic nanoparticles deliver singlet oxygen for mild oxidations: rechargeable, removable, reusable

“…2 While it is possible to chemically generate singlet oxygen by various inorganic reactions, 3 for most applications, including its therapeutic potential, mild methods of generation are preferred, and chief among them is photosensitized generation by making use of photosensitizers with large intersystem crossing efficiency. 4 On the other hand, chemical generation of singlet oxygen requires highly oxidizing agents such as permolybdate 3b or hypervalent iodine. 3d Only known mild chemical reactions rely on thermal cycloreversion reactions of various endoperoxides.…”

“…2 While it is possible to chemically generate singlet oxygen by various inorganic reactions, 3 for most applications, including its therapeutic potential, mild methods of generation are preferred, and chief among them is photosensitized generation by making use of photosensitizers with large intersystem crossing efficiency. 4…”