Modulating absorption and charge transfer in bodipy-carbazole donor–acceptor dyads through molecular design

Strahan, John; Popere, Bhooshan C.; Khomein, Piyachai; Pointer, Craig A.; Martin, Shea M; Oldacre, Amanda N.; Thayumanavan, S.; Young, Elizabeth R.

doi:10.1039/c9dt00094a

Cited by 22 publications

(21 citation statements)

References 79 publications

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“…By contrast, for the smallest active compounds (23), the HOMO and LUMO are almost dispersed across the entire molecular region. These results suggest the most active compounds have acceptor-donator behavior, as reported before in several studies [55][56][57][58][59][60][61][62][63].…”

Section: Molecular Orbitalssupporting

confidence: 87%

Modelling the Anti-Methicillin-Resistant Staphylococcus Aureus (MRSA) Activity of Cannabinoids: A QSAR and Docking Study

2020

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Twenty-four cannabinoids active against MRSA SA1199B and XU212 were optimized at WB97XD/6-31G(d,p), and several molecular descriptors were obtained. Using a multiple linear regression method, several mathematical models with statistical significance were obtained. The robustness of the models was validated, employing the leave-one-out cross-validation and Y-scrambling methods. The entire data set was docked against penicillin-binding protein, iso-tyrosyl tRNA synthetase, and DNA gyrase. The most active cannabinoids had high affinity to penicillin-binding protein (PBP), whereas the least active compounds had low affinities for all of the targets. Among the cannabinoid compounds, Cannabinoid 2 was highlighted due to its suitable combination of both antimicrobial activity and higher scoring values against the selected target; therefore, its docking performance was compared to that of oxacillin, a commercial PBP inhibitor. The 2D figures reveal that both compounds hit the protein in the active site with a similar type of molecular interaction, where the hydroxyl groups in the aromatic ring of cannabinoids play a pivotal role in the biological activity. These results provide some evidence that the anti-Staphylococcus aureus activity of these cannabinoids may be related to the inhibition of the PBP protein; besides, the robustness of the models along with the docking and Quantitative Structure–Activity Relationship (QSAR) results allow the proposal of three new compounds; the predicted activity combined with the scoring values against PBP should encourage future synthesis and experimental testing.

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Section: Molecular Orbitalssupporting

confidence: 87%

Modelling the Anti-Methicillin-Resistant Staphylococcus Aureus (MRSA) Activity of Cannabinoids: A QSAR and Docking Study

2020

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“…Upon chromatography 3-bromo-9-hexylcarbazole (4) was obtained as a liquid in good yield. 3-Bromo-9-hexylcarbazole (4) was then converted into the pinacol boronic ester by treating with bis(pinacolato)diboron in the presence of potassium acetate (KOAc) and dichlorobis(triphenylphosphine)palladium(II) in 1,4-dioxane [36,37]. Upon chromatography (9-hexylcarbazole-3-yl)boronic acid pinacol ester (5) was obtained as a liquid in good yield.…”

Section: Synthesismentioning

confidence: 99%

Synthesis of novel multifunctional carbazole-based molecules and their thermal, electrochemical and optical properties

Altınölçek

Battal

Tavaslı

et al. 2020

Beilstein J. Org. Chem.

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Two novel carbazole-based compounds 7a and 7b were synthesised as potential candidates for application in organic electronics. The materials were fully characterised by NMR spectroscopy, mass spectrometry, FTIR, thermogravimetric analysis, differential scanning calorimetry, cyclic voltammetry, and absorption and emission spectroscopy. Compounds 7a and 7b, both of which were amorphous solids, were stable up to 291 °C and 307 °C, respectively. Compounds 7a and 7b show three distinctive absorption bands: high and mid energy bands due to locally excited (LE) transitions and low energy bands due to intramolecular charge transfer (ICT) transitions. In dichloromethane solutions compounds 7a and 7b gave emission maxima at 561 nm and 482 nm with quantum efficiencies of 5.4% and 97.4% ± 10%, respectively. At positive potential, compounds 7a and 7b gave two different oxidation peaks, respectively: quasi-reversible at 0.55 V and 0.71 V, and reversible at 0.84 V and 0.99 V. At negative potentials, compounds 7a and 7b only exhibited an irreversible reduction peak at −1.86 V and −1.93 V, respectively.

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“…In the absorption spectrum of the BZnTPP film, although the absorption bands of the porphyrin segment are quite distinct and appear at the same wavelengths as in the dilute solution, the band originating from the bodipy segment shows very low intensity and a pronounced red shift of 15 nm (from 500 to 515 nm; Figure S2). This bathochromic shift in the absorption peak of the bodipy segment indicates the formation of charge transfer states between the donor (porphyrin) and acceptor (bodipy) moieties . We then spin-coated BZnTPP from its methanolic solutions on top of the selected metal oxides, i.e., ZnO and TiO 2 , which served as the electron transport materials in OSCs and PSCs, respectively.…”

Section: Resultsmentioning

confidence: 99%

Enhanced Organic and Perovskite Solar Cell Performance through Modification of the Electron-Selective Contact with a Bodipy–Porphyrin Dyad

Gkini

Verykios

Balis

et al. 2019

ACS Appl. Mater. Interfaces

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Photovoltaic devices based on organic semiconductors and organo-metal halide perovskites have not yet reached the theoretically predicted power conversion efficiencies while they still exhibit poor environmental stability. Interfacial engineering using suitable materials has been recognized as an attractive approach to tackle the above issues. We introduce here a zinc porphyrin–triazine–bodipy donor−π bridge–acceptor dye as a universal electron transfer mediator in both organic and perovskite solar cells. Thanks to its “push–pull” character, this dye enhances electron transfer from the absorber layer toward the electron-selective contact, thus improving the device’s photocurrent and efficiency. The direct result is more than 10% average power conversion efficiency enhancement in both fullerene-based (from 8.65 to 9.80%) and non-fullerene-based (from 7.71 to 8.73%) organic solar cells as well as in perovskite ones (from 14.56 to 15.67%), proving the universality of our approach. Concurrently, by forming a hydrophobic network on the surface of metal oxide substrates, it improves the nanomorphology of the photoactive overlayer and contributes to efficiency stabilization. The fabricated devices of both kinds preserved more than 85% of their efficiency upon exposure to ambient conditions for more than 600 h without any encapsulation.

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Modulating absorption and charge transfer in bodipy-carbazole donor–acceptor dyads through molecular design

Abstract: Bodipy-based donor–acceptor dyads were evaluated using transient absorption spectroscopy to reveal the influence of beta vs. meso substitution on excited-state dynamics.

Cited by 22 publications

References 79 publications

Modelling the Anti-Methicillin-Resistant Staphylococcus Aureus (MRSA) Activity of Cannabinoids: A QSAR and Docking Study

Modelling the Anti-Methicillin-Resistant Staphylococcus Aureus (MRSA) Activity of Cannabinoids: A QSAR and Docking Study

Synthesis of novel multifunctional carbazole-based molecules and their thermal, electrochemical and optical properties

Enhanced Organic and Perovskite Solar Cell Performance through Modification of the Electron-Selective Contact with a Bodipy–Porphyrin Dyad

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