4.8 Article

Anthracene-Fused Oligo-BODIPYs: A New Class of π-Extended NIR-Absorbing Materials

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WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202214543

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BODIPY; Conjugation; Dyes/Pigments; NIR; pi-Systems

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In this study, a series of fully pi-conjugated anthracene-fused oligo-BODIPYs were successfully synthesized via Au-I-catalyzed cyclization. The structural and optoelectronic properties of these compounds were studied using various techniques, and their electronic structures were explored through Density Functional Theory calculations. The findings revealed unique features of these compounds, making them valuable for technological applications.
Large pi-conjugated systems are key in the area of molecular materials. Herein, we prepare via Au-I-catalyzed cyclization a series of fully pi-conjugated anthracene-fused oligo-BODIPYs. Their structural and optoelectronic properties were studied by several techniques, ranging from X-ray, UV/Vis, and cyclic voltammetry to transient absorption spectroscopy. As a complement, their electronic structures were explored by means of Density Functional Theory (DFT) calculations. Depending on the size and shape of the pi-conjugated skeleton, unique features-such as face-to-face supramolecular organization, NIR absorption and fluorescence as well as strong electron accepting character-were noted. All in all, the aforementioned features render them valuable for technological applications.

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