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• W3119470003 endingPage "109133" @default.
• W3119470003 startingPage "109133" @default.
• W3119470003 abstract "Herein, the optical properties of thiophene-functionalized quadrupolar carbo-benzenes and a benzenic parent, of generic structure Th–CC–[core]–CC–Th, Th = R2C4HS, are comparatively investigated. Beyond the previously unknown dioctylthienylethynylbenzene (core = p-C6H4, R = nOct), two bis-dialkylthienylethynyl-carbo-benzenes (core = C18Ph4, R = nOct, nBu) are envisaged for the unique carbo-aromatic character of the C18 macrocycle. The three targets were synthesized from the corresponding ethynylthiophenes in 47, 20 and 10% yield, respectively, then characterized by classical methods such as NMR spectroscopy, and X-ray crystallography for one of the carbo-benzenes. Regarding linear and nonlinear optical properties, our results show that the carbo-merization induces a significant shift to lower energies of the one-photon electronic excitations accompanied by an 8-fold increase of the molar extinction coefficient compared to the parent molecule. Intriguingly, these excitations lead to a broad band of photoluminescence comprising decay transitions of the type S1 → S0 but also of the type S2 → S0. This phenomenon of emission from higher excited states, which is contrary to Kasha's rule, is assigned to - or revealed by - a reduction of the internal conversion efficiency between S2 and S1. Two-photon induced transitions are also enhanced, the two-photon absorption cross-section (σ2PA) being in average five times larger for the carbo-benzenes than for their benzene parent in the wavelength range 650–950 nm, with a maximum of σ2PA = 1430 GM (1 GM = 10−50 cm4 s/photon). Beyond a moderate nonlinearity, this comparative study provides quantitative insights about the way carbo-merization or insertion of a π-conjugated macrocycle between chromophoric functions (here thiophene rings) can tune optical properties of organic molecules. The optical properties of the bis-dialkylthienylethynyl-carbo-benzenes are also discussed in regard of recent reports on organic chromophores based on other types of π-conjugated macrocyclic cores." @default.
• W3119470003 created "2021-01-18" @default.
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• W3119470003 date "2021-04-01" @default.
• W3119470003 modified "2023-10-18" @default.
• W3119470003 title "Linear and nonlinear optical properties of a quadrupolar carbo-benzene and its benzenic parent: The carbo-merization effect" @default.
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• W3119470003 doi "https://doi.org/10.1016/j.dyepig.2021.109133" @default.
• W3119470003 hasPublicationYear "2021" @default.
• W3119470003 type Work @default.

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