Expeditious Synthesis of Fluorescent Bis(phenylfuryl)benzenes

Miao Zhang; Tingshu Wang; Chanyoung Boo; Sangho Koo

doi:10.1055/a-1941-1535

Synthesis, Table of Contents

Synthesis 2023; 55(01): 111-120
DOI: 10.1055/a-1941-1535

paper

Expeditious Synthesis of Fluorescent Bis(phenylfuryl)benzenes

Authors

Miao Zhang

^aSchool of Pharmacy, East China University of Science and Technology, Meilong Road 130, Shanghai 200237, P. R. of China

^bDepartment of Energy Science and Technology, Myongji University, Myongji-Ro 116, Cheoin-Gu, Yongin, Gyeonggi-Do 17058, Korea
Tingshu Wang

^aSchool of Pharmacy, East China University of Science and Technology, Meilong Road 130, Shanghai 200237, P. R. of China

^bDepartment of Energy Science and Technology, Myongji University, Myongji-Ro 116, Cheoin-Gu, Yongin, Gyeonggi-Do 17058, Korea
Chanyoung Boo

^cDepartment of Chemistry, Myongji University, Myongji-Ro 116, Cheoin-Gu, Yongin, Gyeonggi-Do 17058, Korea
Sangho Koo ∗

^aSchool of Pharmacy, East China University of Science and Technology, Meilong Road 130, Shanghai 200237, P. R. of China

^bDepartment of Energy Science and Technology, Myongji University, Myongji-Ro 116, Cheoin-Gu, Yongin, Gyeonggi-Do 17058, Korea

^cDepartment of Chemistry, Myongji University, Myongji-Ro 116, Cheoin-Gu, Yongin, Gyeonggi-Do 17058, Korea

Abstract

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This paper is dedicated to Professor Masato Koreeda on the occasion of his 80^th birthday.

Abstract

Versatile fluorescent polyaromatic compounds of alternating benzene and furan rings, para- and meta-bis(5-phenylfur-3-yl)benzenes, were expeditiously synthesized by double Mn(OAc)₃-catalyzed oxidative decarbonylation and Paal–Knorr reactions of β-ketoesters, prepared from the conjugate addition of ethyl acetoacetate to para- and meta-bis(chalcones). Stronger fluorescence intensity was observed for meta-bis(phenylfuryl)benzene with ortho-methoxy substitution, whereas longer fluorescence wavelength was observed for para-bis(phenylfuryl)benzene with para-methoxy substitution.

Key words

arenes - cyclization - radical reactions - fluorescence - manganese

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References

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Supplementary Material

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