BODIPY parent compound: Fluorescence, singlet oxygen formation and properties revealed by DFT calculations

Zhang, Xianfu; Zhu, Jiale

doi:10.1016/j.jlumin.2018.09.017

Cited by 24 publications

(20 citation statements)

References 25 publications

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“…This indicates only a small change in dipole moment (or geometry) in transition from the ground to the excited state (Luo et al, 2015b). The fluorescence quantum yield for the monomer is high ( fl = 92% Table 1), in agreement with the literature (Ulrich et al, 2008;Zhang and Zhu, 2019). The UV spectrum of FIGURE 3 | Normalised absorption spectra for monomer (solid red), polymer (solid blue) and normalised emission spectra for monomer (dashed red) and polymer (dashed blue).…”

Section: Uv-visible and Emission Spectroscopysupporting

confidence: 82%

“…BODIPY dyes ( Figure 1A) are one of the most extensively studied chromophores in recent years, due to ease of synthesis, thermal stability and solubility in a range of organic solvents (Wan et al, 2003;Azov et al, 2005;Ziessel et al, 2005;Kim et al, 2006;Loudet and Burgess, 2007). A variety of BODIPY architectures have been developed, involving substitution at the meso position, the pyrrole unit (β position), the boron atom, as well as post-functionalisation and polymerisation at the periphery of the chromophore ( Figure 1B) (Ulrich et al, 2008;Boens et al, 2015Boens et al, , 2019Zhao et al, 2015;Zhang and Zhu, 2019).…”

Section: Introductionmentioning

confidence: 99%

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A Time-Resolved Spectroscopic Investigation of a Novel BODIPY Copolymer and Its Potential Use as a Photosensitiser for Hydrogen Evolution

et al. 2020

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A novel 4,4-difuoro-4-bora-3a,4a-diaza-s-indacene (BODIPY) copolymer with diethynylbenzene has been synthesised, and its ability to act as a photosensitiser for the photocatalytic generation of hydrogen was investigated by time-resolved spectroscopic techniques spanning the ps-to ns-timescales. Both transient absorption and time-resolved infrared spectroscopy were used to probe the excited state dynamics of this photosensitising unit in a variety of solvents. These studies indicated how environmental factors can influence the photophysics of the BODIPY polymer. A homogeneous photocatalytic hydrogen evolution system has been developed using the BODIPY copolymer and cobaloxime which provides hydrogen evolution rates of 319 µmol h −1 g −1 after 24 h of visible irradiation.

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Section: Uv-visible and Emission Spectroscopysupporting

confidence: 82%

Section: Introductionmentioning

confidence: 99%

A Time-Resolved Spectroscopic Investigation of a Novel BODIPY Copolymer and Its Potential Use as a Photosensitiser for Hydrogen Evolution

et al. 2020

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“…Photosensitizers (PSs) which efficiently form long-lived triplet excited states are crucially important in such fields as photoredox catalysis, 1 photodynamic therapy (PDT) 2 and triplettriplet annihilation upconversion. 3 Common approach for enhancing the triplet state yield ( T ) in organic chromophores relies on the introduction of heavy atoms, such as halogens (Br or I) or transition metals (e.g., Ru, Pd or Pt) in the structure (Figure 1A), which promote the intersystem crossing process via spin-orbit coupling interactions.…”

Section: Introductionmentioning

confidence: 99%

Quantitative Structure‐Property Relationship Modelling for the Prediction of Singlet Oxygen Generation by Heavy‐Atom‐Free BODIPY Photosensitizers**

Buglak

Charisiadis

Sheehan

et al. 2021

Chemistry A European J

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Section: Introductionmentioning

confidence: 99%

“…Seemingly, in the case of 64 the descriptor evaluates the frequency of pairs between nitrogen atoms and methyl groups.F03[C-N] (α = -20.2) is a frequency of C and N atoms at a topological distance of 3. The higher the value of the descriptor, the lower the quantum yield of1 O 2 generation. Parent BODIPY 1 has the lowest value of F03[C-N] equal to 4, whereas dimer 46 possesses the highest value of 24.…”

mentioning

confidence: 99%

Quantitative Structure–property Relationship Modelling for the Prediction of Singlet Oxygen Generation by Heavy-Atom-Free BODIPY Photosensitizers

Buglak¹,

Charisiadis²,

Sheehan³

et al. 2021

Preprint

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Heavy-atom-free sensitizers forming long-living triplet excited states via the spin-orbit charge transfer intersystem crossing (SOCT-ISC) process have recently attracted attention due to their potential to replace costly transition metal complexes in photonic applications. The efficiency of SOCT-ISC in BODIPY donor-acceptor dyads, so far the most thoroughly investigated class of such sensitizers, can be finely tuned by structural modification. However, predicting the triplet state yields and reactive oxygen species (ROS) generation quantum yields for such compounds in a particular solvent is still very challenging due to a lack of established quantitative structure-property relationship (QSPR) models. Herein, we analyzed the available data on singlet oxygen generation quantum yields (F?) for a dataset containing > 70 heavy-atom-free BODIPY in three different solvents (toluene, acetonitrile, and tetrahydrofuran). In order to build reliable QSPR model, we synthesized a series of new BODIPYs containing different electron donating aryl groups in the meso position, studied their optical and structural properties along with the solvent dependence of singlet oxygen generation, which confirmed the formation of triplet states via the SOCT-ISC mechanism. For the combined dataset of BODIPY structures, a total of more than 5000 quantum-chemical descriptors was calculated including quantum-chemical descriptors using Density Functional Theory (DFT), namely M06-2X functional. QSPR models predicting F? values were developed using multiple linear regression (MLR), which perform significantly better than other machine learning methods and show sufficient statistical parameters (R = 0.88 ? 0.91 and q2 = 0.62 ? 0.69) for all three solvents. A small root mean squared error of 8.2% was obtained for F? values predicted using MLR model in toluene. As a result, we proved that QSPR and machine learning techniques can be useful for predicting F? values in different media and virtual screening of new heavy-atom-free BODIPYs with improved photosensitizing ability.<br>

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BODIPY parent compound: Fluorescence, singlet oxygen formation and properties revealed by DFT calculations

Cited by 24 publications

References 25 publications

A Time-Resolved Spectroscopic Investigation of a Novel BODIPY Copolymer and Its Potential Use as a Photosensitiser for Hydrogen Evolution

A Time-Resolved Spectroscopic Investigation of a Novel BODIPY Copolymer and Its Potential Use as a Photosensitiser for Hydrogen Evolution

Quantitative Structure‐Property Relationship Modelling for the Prediction of Singlet Oxygen Generation by Heavy‐Atom‐Free BODIPY Photosensitizers**

Quantitative Structure–property Relationship Modelling for the Prediction of Singlet Oxygen Generation by Heavy-Atom-Free BODIPY Photosensitizers

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