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Extended Benzene-Fused Oligo-BODIPYs: In Three Steps to a Series of Large, Arc-Shaped, Near-Infrared Dyes.

ABSTRACT: We present a straightforward, three-step synthesis engaging an oligomerization and subsequent one-pot oxidation step to form fully conjugated, benzene-fused oligo-BODIPYs from simple BODIPY precursors. FeCl₃ serves as an efficient, bifunctional oxidant for a (multiple) cyclization/desaturation process, applied to ethylene-bridged dimeric, trimeric and oligomeric species to transform linking ethano units into stiff benzene fusions between unsubstituted ?-positions of each BODIPY unit. The structural integrity was verified by X-ray crystallography, and all target compounds were studied in detail by photophysical, electrochemical and computational means. The main S₁ excited state gradually converges to a structure-specific excitation limit, displaying a strong shift of the absorption event from about 500?nm (BODIPY monomer) to 955?nm (octamer) with attenuation coefficients up to ca. 500?000?M^-1 ?cm^-1 .

SUBMITTER: Patra A

PROVIDER: S-EPMC7839587 | biostudies-literature | 2020 Oct

REPOSITORIES: biostudies-literature

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Extended Benzene-Fused Oligo-BODIPYs: In Three Steps to a Series of Large, Arc-Shaped, Near-Infrared Dyes.

Patra Atanu A Patalag Lukas J LJ Jones Peter G PG Werz Daniel B DB

Angewandte Chemie (International ed. in English) 20201109 2

We present a straightforward, three-step synthesis engaging an oligomerization and subsequent one-pot oxidation step to form fully conjugated, benzene-fused oligo-BODIPYs from simple BODIPY precursors. FeCl<sub>3</sub> serves as an efficient, bifunctional oxidant for a (multiple) cyclization/desaturation process, applied to ethylene-bridged dimeric, trimeric and oligomeric species to transform linking ethano units into stiff benzene fusions between unsubstituted β-positions of each BODIPY unit. ...[more]

PMID: 33022876

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