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Covalently linked dimer of chlorophyll-a derivative with an amide bond and its folded conformer

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Abstract A chlorophyll-a derivative homo-dimer covalently linked with a flexible methylene-amino-methylene group at the 3-position was benzoylated to give the dyad bearing a CH2N(COPh)CH2 linker. The synthetic dyad with the… Click to show full abstract

Abstract A chlorophyll-a derivative homo-dimer covalently linked with a flexible methylene-amino-methylene group at the 3-position was benzoylated to give the dyad bearing a CH2N(COPh)CH2 linker. The synthetic dyad with the relatively rigid spacer showed red-shifted visible absorption bands and was oxidized more readily, in comparison with the corresponding monomer. The optical and electrochemical properties of the dimer are ascribable to the partial π-stacking of chlorin moieties in the benzoylated dyad, mimicking the special dimeric species in reaction centers of photochemical systems in natural phototrophs.

Keywords: dimer chlorophyll; chlorophyll derivative; linked dimer; covalently linked

Journal Title: Tetrahedron Letters
Year Published: 2018

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