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분자활성 촉매반응 연구단
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3,5-Diarylimidazo[1,2-a]pyridines as Color-Tunable Fluorophores

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Title
3,5-Diarylimidazo[1,2-a]pyridines as Color-Tunable Fluorophores
Author(s)
Ju Young Lee; Jae Yul Shim; Hong Ki Kim; Donguk Ko; Mu-Hyun Baik; Eun Jeong Yoo
Publication Date
2017-04
Journal
JOURNAL OF ORGANIC CHEMISTRY, v.82, no.8, pp.4352 - 4361
Publisher
AMER CHEMICAL SOC
Abstract
A new protocol for the synthesis of color-tunable fluorescent 3,5-diarylimidazo[1,2-a]pyridines has been achieved via palladium-catalyzed C-H amination of pyridinium zwitterions. Based on experimental results and computational analysis, we extracted a high correlation of photophysical properties with the theoretical concept and predicted emission wavelengths of 3,5-diarylimidazo[1,2-a]pyridines. The emission wavelengths of imidazo[1,2-a]pyridines increase as a function of the electron-withdrawing nature of the substituent on the C5-aryl group of imidazo[1,2-a]pyridine as a result of inductive effects on the LUMO levels. Varying the substituent on the C3-aryl group imidazo[1,2-a]pyridine changes the HOMO levels. Combining these two sites, the HOMO and LUMO levels can be tuned fairly decoupled from each other. This conceptual trend is demonstrated across a series where the C3 and C5 positions were functionalized independently and then utilizes a combination strategy where both sites are used to prepare fluorophores with a large window of emission wavelengths. In view of the biological properties of imidazo[1,2-a]pyridines, the developed method provides an efficient approach for understanding and preparing strongly fluorescent bioprobes. © 2017 American Chemical Society
URI
https://pr.ibs.re.kr/handle/8788114/3731
ISSN
0022-3263
Appears in Collections:
Center for Catalytic Hydrocarbon Functionalizations(분자활성 촉매반응 연구단) > Journal Papers (저널논문)
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