Highly crystalline and fluorescent BODIPY-labelled phenyl-triazole-coumarins as n-type semiconducting materials for OFET devices

Emilio de la Cerda-Pedro, José; Hernández-Ortiz, Oscar Javier; Vázquez-García, Rosa Angeles; García-Báez, Efrén V.; Gómez-Aguilar, Ramón; Espinosa-Roa, Arián; Farfán, Norberto; Padilla-Martínez, Itzia I.

doi:10.1016/j.heliyon.2023.e23517

Heliyon

2024

DOI: 10.1016/j.heliyon.2023.e23517

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Highly crystalline and fluorescent BODIPY-labelled phenyl-triazole-coumarins as n-type semiconducting materials for OFET devices

José Emilio de la Cerda-Pedro,

Oscar Javier Hernández-Ortiz,

Rosa Angeles Vázquez-García

et al.

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2024

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Cited by 2 publications

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Introducing of an Unexplored Aza-BODIPY Diradicaloids with 4-(2,6-Ditert-butyl)phenoxyl Radicals Located in 1,7-Positions of the Aza-BODIPY Core

Oyelowo,

Schaffner,

Jeaydi

et al. 2024

Inorg. Chem.

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We have prepared and characterized two diradicaloid systems 5a and 5b that originated from the oxidation of a 1,7-(4-(2,6-di-tert-butyl)phenol)-substituted aza-BODIPY core. The aza-BODIPY diradicaloids were characterized by a large array of experimental and computational methods. The diamagnetic closed-shell state was postulated as the ground state in solution and a solid-state with the substantial thermal population originating from both open-shell diradical and open-shell triplet states observed at room temperature. Transient absorption spectroscopy indicates fast (<10 ps) excited state deactivation pathways associated with the target compounds' diradical character in solution at room temperature. Variable-temperature 1 H NMR spectra indicate the solvent dependency of the diradical character in 5a and 5b. The diradicaloids could be stepwise reduced to the mixed-valence radical-anion and dianion states upon consequent single-electron reductions. Similarly, deprotonated 1,7-(4-(2,6-di-tert-butyl)phenol)-substituted aza-BODIPYs can be oxidized to the diradicaloid form. Both mixed-valence and dianionic forms exhibit an intense absorption in the NIR region. Density functional theory (DFT) and time-dependent DFT calculations were used to explain the transformations in the UV−Vis-NIR spectra of all target compounds.

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Introducing of an Unexplored Aza-BODIPY Diradicaloids with 4-(2,6-Ditert-butyl)phenoxyl Radicals Located in 1,7-Positions of the Aza-BODIPY Core

Oyelowo,

Schaffner,

Jeaydi

et al. 2024

Inorg. Chem.

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Synthesis of Unsymmetrically Condensed Benzo- and Thienotriazologermoles

Wang,

Adachi,

Ohshita

2024

Molecules

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Germoles and siloles unsymmetrically condensed with heteroaromatic units are attracting much interest. In this study, compounds containing a triazologermole core unit condensed with a benzene or thiophene ring were prepared. Thienotriazologermole was subjected to bromination to obtain the bromide, which underwent transformation via the palladium-catalyzed Stille coupling reaction to form triphenylamine-substituted thienotriazolegermole, with an effective extension of conjugation. The electronic states and properties of these triazologermole derivatives are discussed on the basis of optical and electrochemical measurements and density functional theory calculations. Triphenylamine-substituted thienotriazolegermole showed clear solvatochromic properties in photoluminescence measurements, suggesting that intramolecular charge transfer occurs at the photo-excited state. This clearly indicates that the triazologermole unit is useful as an acceptor of donor–acceptor compounds. The potential application of triphenylamine-substituted thienotriazolegermole as a sensing material was also explored.

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Highly crystalline and fluorescent BODIPY-labelled phenyl-triazole-coumarins as n-type semiconducting materials for OFET devices

Cited by 2 publications

References 97 publications

Introducing of an Unexplored Aza-BODIPY Diradicaloids with 4-(2,6-Ditert-butyl)phenoxyl Radicals Located in 1,7-Positions of the Aza-BODIPY Core

Introducing of an Unexplored Aza-BODIPY Diradicaloids with 4-(2,6-Ditert-butyl)phenoxyl Radicals Located in 1,7-Positions of the Aza-BODIPY Core

Synthesis of Unsymmetrically Condensed Benzo- and Thienotriazologermoles

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