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Issue 1, 2017
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Synthesis and properties of [8]-, [10]-, [12]-, and [16]cyclo-1,4-naphthylenes

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Abstract

The synthesis and properties of various [n]cyclo-1,4-naphthylenes ([n]CNs, n = 8, 10, 12, and 16) are described. Initially, extended L-shaped units, which could be converted into quater- or quinquenaphthylenes were prepared. Nickel- or palladium-mediated couplings of these extended L-shaped units, followed by reductive aromatization of the coupling products afforded [8]-, [10]-, [12]-, and [16]CNs. The size-dependent photophysical properties of these CNs were confirmed by measuring their UV-vis absorption and fluorescence spectra. The theoretical studies supported substantial effects of the number of naphthalene rings on the structural and photophysical properties of these CNs. A kinetic study on the thermal conversion of the Cs-symmetric conformer of [10]CN into its most stable D5d-symmetric conformer indicated that ring strain affects the rotation barrier of the naphthalene rings in [10]CN.

Graphical abstract: Synthesis and properties of [8]-, [10]-, [12]-, and [16]cyclo-1,4-naphthylenes

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Publication details

The article was received on 09 Sep 2016, accepted on 11 Sep 2016 and first published on 12 Sep 2016


Article type: Edge Article
DOI: 10.1039/C6SC04048A
Citation: Chem. Sci., 2017,8, 661-667
  • Open access: Creative Commons BY license
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    Synthesis and properties of [8]-, [10]-, [12]-, and [16]cyclo-1,4-naphthylenes

    K. Okada, A. Yagi, Y. Segawa and K. Itami, Chem. Sci., 2017, 8, 661
    DOI: 10.1039/C6SC04048A

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