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

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A new protocol for the synthesis of color-tunable fluorescent 3,S-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 3,5diarylimidazo [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 CS-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 CS 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.
Publisher
AMER CHEMICAL SOC
Issue Date
2017-04
Language
English
Article Type
Article
Keywords

ONE-POT SYNTHESIS; C-H AMINATION; DENSITY-FUNCTIONAL THEORY; EFFECTIVE CORE POTENTIALS; SOLVATION FREE-ENERGIES; MOLECULAR CALCULATIONS; COMBINATORIAL DISCOVERY; CYCLOADDITION REACTIONS; COUPLING REACTIONS; AZOMETHINE YLIDES

Citation

JOURNAL OF ORGANIC CHEMISTRY, v.82, no.8, pp.4352 - 4361

ISSN
0022-3263
DOI
10.1021/acs.joc.7b00358
URI
http://hdl.handle.net/10203/223916
Appears in Collection
CH-Journal Papers(저널논문)
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