High singlet oxygen production and negative solvatochromism of octabrominated 3-pyrrolyl boron dipyrromethenes

Abstract

The newly synthesized and structurally characterized octabrominated 3-pyrrolyl boron dipyrromethenes is shown reveal negative solvatochromism, and quantitative generation of singlet oxygen; properties relevant to develop new PDT agents.

Modulation of singlet oxygen generation in halogenated BODIPY dyes by substitution at their meso position: towards a solvent-independent standard in the vis region

“…Br, I) directly to the BODIPY core, thereby favoring spin-orbit coupling. 6,[10][11][12][13] Indeed, the in vitro or in vivo tests have already showed the efficacy of halogenated BODIPYs to kill tumor cells. 14 In this work new halogenated-BPD with different substitution patterns at their meso position are studied (Scheme 1).…”

Strongly Coupled Oxasmaragdyrin–BF2 Chelated Dipyrrin Dyads: Syntheses, X‐ray Structure, Ground‐ and Excited‐State Charge‐Transfer Interactions

“…[71,72] Furthermore, BODIPYs are easily amenable to structural modifications, hence the electronic properties of thesed yes can be fine-tuned at will by introducing appropriate substituents on the BODIPY core. [73][74][75] In this regard, we recently reported the facile synthesis of 3-pyrrolyl BODIPYs (pyrBODIPY)i nw hicht he spectrala nd electrochemical studies showedt hat the presence of pyrrolyl group at the a-position of BODIPY significantly alters the electronic properties. [76] In addition, the appended pyrrole ring on the BODIPY is easy to functionalize and the functionalized 3-pyrrolyl BODIPYsc an be used as synthons to prepares everal interesting fluorescent compounds with variety of applications.…”

“…The excellent photophysical properties, such as long absorption and fluorescence wavelengths, high extinction coefficients, high fluorescence quantum yields, decent singlet state lifetimes and high photostability of BF 2 ‐dipyrrins, are some of the key features that attracted researchers to widely use these dyes as biomolecular labels, chromogenic probes, drug‐delivery agents, fluorescent switches, electroluminescent films, laser dyes, light‐harvesters, sensitizers for solar cells and ion sensors . Furthermore, BODIPYs are easily amenable to structural modifications, hence the electronic properties of these dyes can be fine‐tuned at will by introducing appropriate substituents on the BODIPY core . In this regard, we recently reported the facile synthesis of 3‐pyrrolyl BODIPYs (pyrBODIPY) in which the spectral and electrochemical studies showed that the presence of pyrrolyl group at the α‐position of BODIPY significantly alters the electronic properties .…”

Copper-catalyzed alkyne oxidation/Büchner-type ring-expansion to access benzo[6,7]azepino[2,3-b]quinolines and pyridine-based diones

“…9d ). Interestingly, the 3r displayed negative solvatochromism 59 – 61 , and the emissions of 3r were blue-shifted from 537 to 423 nm by increasing solvent polarity (the structures of the 3r were optimized and the dipole moment of 3r in the excited and ground states were calculated by Gaussian 09 at the B3LYP/6-31G(d) level). The ground state of 3r was calculated to be slightly more polar (Dipole Moment = 7.28 Debye) than the excited state (Dipole Moment = 6.45 Debye).…”