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

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 C_s-symmetric conformer of [10]CN into its most stable D_5d-symmetric conformer indicated that ring strain affects the rotation barrier of the naphthalene rings in [10]CN.

SUBMITTER: Okada K

PROVIDER: S-EPMC5297897 | biostudies-literature | 2017 Jan

REPOSITORIES: biostudies-literature

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

Okada Keishu K Yagi Akiko A Segawa Yasutomo Y Itami Kenichiro K

Chemical science 20160912 1

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 me ...[more]

PMID: 28451214

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