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Synthesis 2021; 53(18): 3355-3360
DOI: 10.1055/a-1516-9399
special topic
Bond Activation – in Honor of Prof. Shinji Murai

Strategic Synthesis of Asymmetrically Substituted C4N4 Fluorophores

Wei Xu 
a   Institute of Microbial Chemistry, 3-14-23 Kamiosaki, Shinagawa-ku, Tokyo 141-0021, Japan
,
Miki Kohei
b   Faculty of Pharmacy, Keio University, 1-5-30 Shibakoen, Minato-ku, Tokyo 105-8512, Japan
,
Masakatsu Shibasaki  ∗
a   Institute of Microbial Chemistry, 3-14-23 Kamiosaki, Shinagawa-ku, Tokyo 141-0021, Japan
,
Naoya Kumagai  ∗
a   Institute of Microbial Chemistry, 3-14-23 Kamiosaki, Shinagawa-ku, Tokyo 141-0021, Japan
b   Faculty of Pharmacy, Keio University, 1-5-30 Shibakoen, Minato-ku, Tokyo 105-8512, Japan
› Author AffiliationsThis work was financially supported by the Japan Society for the Promotion of Science (JSPS) KAKENHI [Grant Numbers JP19K22192 (Grant-in-Aid for Exploratory Research, to N.K.) and JP20H02746 (Grant-in-Aid for Scientific Research (B)), to N.K.]. N.K. also thanks the Japan Agency for Medical Research and Development (AMED) (Grant Number JP21wm0325008) for financial support.
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Abstract

C4N4 fluorophores comprise a recently disclosed new class of emissive organic molecules with modular synthetic capabilities. Herein, we report a new synthetic protocol toward asymmetrically di­arylated C4N4 fluorescent materials. Direct monoarylation of 1-naphthol is exploited to suppress undesired diarylation and to provide a free phenolic hydroxy group for prospective linking to a molecule of interest. Installation of the second aromatic unit in order to acquire fluorescent properties is achieved by Suzuki–Miyaura cross-coupling.

Key words

fluorescence - pyrimidine - quantum yield - aluminum - direct arylation - C4N4 fluorophore - fluorescent probe

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/a-1516-9399.
  • Supporting Information


Publication History

Received: 08 May 2021

Accepted after revision: 25 May 2021

Accepted Manuscript online:
25 May 2021

Article published online:
24 June 2021

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