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Development of New Pyrrolocoumarin Derivatives with Satisfactory Fluorescent Properties and Notably Large Stokes Shifts
Author(s) -
Chen Lei,
Hu TaiShan,
Yao ZhuJun
Publication year - 2008
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200800883
Subject(s) - fluorescence , stokes shift , chemistry , förster resonance energy transfer , molecule , wavelength , fluorescence in the life sciences , biological imaging , nanotechnology , photochemistry , combinatorial chemistry , organic chemistry , optoelectronics , optics , materials science , physics
Small, organic, fluorescent molecules with large Stokes shifts and long emission wavelengths are ideal dyes for various modern fluorescent imaging technologies such as FRET. In this study, we designed and synthesized a number of new fluorescent molecules on the basic structures of two pyrrolocoumarin skeletons where Fischer's indole synthesis and the Suzuki coupling successfully served as the efficient molecular editing protocols. The examination of the fluorescent properties and further structural optimization of these compounds afforded three new pyrrolocoumarin dyes with notably large Stokes shifts and satisfactory fluorescent properties. Among these, 30 showed a large Stokes shift (113 nm) and intense fluorescence ( φ = 0.55, λ em = 523 nm), and thus showed great potential in biological imaging studies. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)