Visibly Emissive and Responsive Extended 6-Aza-Uridines | Zendy

Patrycja A. Hopkins | Zendy; Renatus W. Sinkeldam | Zendy; Yitzhak Tor | Zendy

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Visibly Emissive and Responsive Extended 6-Aza-Uridines

Author(s) -

Patrycja A. Hopkins,

Renatus W. Sinkeldam,

Yitzhak Tor

Publication year - 2014

Publication title -

organic letters

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.94

H-Index - 239

eISSN - 1523-7060

pISSN - 1523-7052

DOI - 10.1021/ol502435d

Subject(s) - bathochromic shift , chemistry , solvatochromism , conjugated system , aryl , derivative (finance) , photochemistry , combinatorial chemistry , stereochemistry , molecule , organic chemistry , fluorescence , alkyl , polymer , economics , physics , quantum mechanics , financial economics

A family of extended 5-modified-6-aza-uridines was obtained via Suzuki coupling reactions with a common brominated precursor. Extending the conjugated-6-aza-uridines with substituted aryl rings increases the push-pull interactions yielding enhanced bathochromic shifts and solvatochromism compared to the parent nucleosides. For example, the methoxy substituted derivative 1d displays λmax abs around 375 nm, with visible emission maxima at 486 nm (Φ = 0.74) and 525 nm (Φ = 0.02) in dioxane and water, respectively.

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