Abstract

Derivatization of primary amines such as amino acids and peptides with naphthalenedialdehyde (NDA) in the presence of cyanide ion yields cyanobenzo[f]-isoindole (CBI) adducts that are highly fluorescent. However, the fluorescence is seriously quenched with amines that possess more than one primary amine site, as is the case with lysine. Although it was found that the adsorption of CBI₂-lysine on a solid substrate restored the fluorescence, the reason for the solution quenching, with respect to results for mono-derivatized amines, was investigated. The experiments to probe the quenching were based on the assumption that the mechanism responsible for quenching involved a charge-transfer (CT) excited state. Thus, it was found that the solvent properties of viscosity and polarity affected the lifetime and quantum yield of fluorescence in a manner consistent with the proposed mechanism.

Fluorescence thermometers using intramolecular exciplexes

Henry E. Gossage and L. A. Melton
Appl. Opt. 26(11) 2256-2259 (1987)

Towards in vivo imaging of intramolecular fluorescence resonance energy transfer parameters

Vaibhav Gaind, Kevin J. Webb, Sumith Kularatne, and Charles A. Bouman
J. Opt. Soc. Am. A 26(8) 1805-1813 (2009)

Deep-tissue imaging of intramolecular fluorescence resonance energy-transfer parameters

Vaibhav Gaind, Sumith Kularatne, Philip S. Low, and Kevin J. Webb
Opt. Lett. 35(9) 1314-1316 (2010)

Detection of oxygen by fluorescence quenching

M. E. Cox and B. Dunn
Appl. Opt. 24(14) 2114-2120 (1985)

Enhanced optical limiting in derivatized fullerenes

L. Smilowitz, D. McBranch, V. Klimov, J. M. Robinson, A. Koskelo, M. Grigorova, B. R. Mattes, H. Wang, and F. Wudl
Opt. Lett. 21(13) 922-924 (1996)