Strategic Synthesis of Asymmetrically Substituted C4N4 Fluorophores

Wei Xu; Miki Kohei; Masakatsu Shibasaki; Naoya Kumagai

doi:10.1055/a-1516-9399

Strategic Synthesis of Asymmetrically Substituted C4N4 Fluorophores

Wei Xu, Miki Kohei, Masakatsu Shibasaki, Naoya Kumagai

School of Pharmaceutical Sciences

Research output: Contribution to journal › Article › peer-review

1 Citation (Scopus)

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 di arylated 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.

Original language	English
Pages (from-to)	3355-3360
Number of pages	6
Journal	Synthesis (Germany)
Volume	53
Issue number	18
DOIs	https://doi.org/10.1055/a-1516-9399
Publication status	Published - 2021 Sept 16

Keywords

C4N4 fluorophore
aluminum
direct arylation
fluorescence
fluorescent probe
pyrimidine
quantum yield

ASJC Scopus subject areas

Catalysis
Organic Chemistry

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10.1055/a-1516-9399

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title = "Strategic Synthesis of Asymmetrically Substituted C4N4 Fluorophores",

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 di arylated 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.",

keywords = "C4N4 fluorophore, aluminum, direct arylation, fluorescence, fluorescent probe, pyrimidine, quantum yield",

author = "Wei Xu and Miki Kohei and Masakatsu Shibasaki and Naoya Kumagai",

note = "Funding Information: This 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. JapanSocietyforhePomotionofScienceJP19K22192JapanSocietyforthePomoionofScience(JP20H02746)JapanAgencyforMedical ReeachandDevelopmentJP21wm0325008) Publisher Copyright: {\textcopyright} 2021 Georg Thieme Verlag. All rights reserved.",

year = "2021",

month = sep,

day = "16",

doi = "10.1055/a-1516-9399",

language = "English",

volume = "53",

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journal = "Synthesis (Germany)",

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TY - JOUR

T1 - Strategic Synthesis of Asymmetrically Substituted C4N4 Fluorophores

AU - Xu, Wei

AU - Kohei, Miki

AU - Shibasaki, Masakatsu

AU - Kumagai, Naoya

N1 - Funding Information: This 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. JapanSocietyforhePomotionofScienceJP19K22192JapanSocietyforthePomoionofScience(JP20H02746)JapanAgencyforMedical ReeachandDevelopmentJP21wm0325008) Publisher Copyright: © 2021 Georg Thieme Verlag. All rights reserved.

PY - 2021/9/16

Y1 - 2021/9/16

N2 - 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 di arylated 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.

AB - 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 di arylated 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.

KW - C4N4 fluorophore

KW - aluminum

KW - direct arylation

KW - fluorescence

KW - fluorescent probe

KW - pyrimidine

KW - quantum yield

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JO - Synthesis (Germany)

JF - Synthesis (Germany)

IS - 18

ER -

Strategic Synthesis of Asymmetrically Substituted C4N4 Fluorophores

Abstract

Keywords

ASJC Scopus subject areas

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