Issue 1, 2017

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


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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Article type
Edge Article
09 Sep 2016
11 Sep 2016
First published
12 Sep 2016
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY license

Chem. Sci., 2017,8, 661-667

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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