Synlett 2023; 34(12): 1433-1436
DOI: 10.1055/a-2009-8219
cluster
Special Issue Honoring Masahiro Murakami’s Contributions to Science

Synthesis and Properties of Methylene-Bridged [6]Cyclo-2,6-naphthylene

Nobushige Kai
a   Graduate School of Science, Nagoya University, Chikusa, Nagoya 464-8602, Japan
,
Hideya Kono
a   Graduate School of Science, Nagoya University, Chikusa, Nagoya 464-8602, Japan
,
Akiko Yagi
a   Graduate School of Science, Nagoya University, Chikusa, Nagoya 464-8602, Japan
b   Institute of Transformative Bio-Molecules (WPI-ITbM), Nagoya University, Chikusa, Nagoya 464-8602, Japan
,
a   Graduate School of Science, Nagoya University, Chikusa, Nagoya 464-8602, Japan
b   Institute of Transformative Bio-Molecules (WPI-ITbM), Nagoya University, Chikusa, Nagoya 464-8602, Japan
› Author Affiliations
This work was supported by JSPS KAKENHI (grants nos. 19H05463 to K.I., and 19K15537 and 22K14677 to A.Y.) and by CREST (JPMJCR19R1 to A.Y.) and PRESTO (JPMJPR22Q9 to A.Y.) programs from JST.


Abstract

A novel structurally constrained nanobelt, methylene-bridged [6]cyclo-2,6-naphthylene ([6]MCN), has been synthesized by the nickel-mediated intramolecular aryl–aryl coupling of a triflated prism[6]arene. The structural and electronic properties of [6]MCN were revealed through NMR studies and photophysical measurements. In contrast to methylene-bridged [6]cycloparaphenylene, our previously synthesized benzene-based analogue, [6]MCN has a low strain energy (77.4 kcal·mol–1) and displays bright fluorescence (Φ = 0.20).

Supporting Information



Publication History

Received: 01 December 2022

Accepted after revision: 09 January 2023

Accepted Manuscript online:
09 January 2023

Article published online:
02 February 2023

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