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Issue 30, 2018
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Multichromophore arrays of dibenzotetraaza[14]annulene: a promising platform for bioorganic chemistry

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Abstract

The first series of discrete multichromophore arrays of dibenzotetraaza[14]annulene (DBTAA), containing flexible bridges, have been synthesized in 40–46% isolated yields. The key asymmetrical intermediates, carrying two distinctly addressable functionalities (ROH vs. ROCH2–C[triple bond, length as m-dash]C–H and R(CH2)nBr vs. ROCH2–C[triple bond, length as m-dash]C–H) at the macrocycle periphery, were synthesized in moderate to high (30–78%) isolated yields. Facile synthetic protocols developed for the synthesis of discrete DBTAA arrays offer several advantages such as operational simplicity and easy post-synthetic workup that overcome the need for laborious chromatographic purification. All new compounds were characterized by microanalysis, mass spectrometry, UV-Vis, FTIR-ATR, and 1H and 13C NMR spectroscopy. Structural features were briefly discussed with emphasis on several potential applications.

Graphical abstract: Multichromophore arrays of dibenzotetraaza[14]annulene: a promising platform for bioorganic chemistry

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Publication details

The article was received on 08 May 2018, accepted on 11 Jul 2018 and first published on 11 Jul 2018


Article type: Paper
DOI: 10.1039/C8OB01078A
Citation: Org. Biomol. Chem., 2018,16, 5508-5516
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    Multichromophore arrays of dibenzotetraaza[14]annulene: a promising platform for bioorganic chemistry

    K. M. Zwoliński and J. Eilmes, Org. Biomol. Chem., 2018, 16, 5508
    DOI: 10.1039/C8OB01078A

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