Ninhydrin developed fingerprints can be enhanced by treatment with a zinc o
r cadmium salt. The resulting fingerprint luminescence has been attributed
to the induced coplanarity of the bicyclic indanedione rings of Ruhemann's
purple due to complexation with the metal ions. This paper explores whether
this effect also occurs in the 1,8-diaza-9-fluorenone (DFO)-amino acid add
uct (1), formed from the reaction of DFO with amino acids. Molecular modeli
ng studies of (1) indicate a relatively small out-of-plane angle of 24 degr
ees. H-1 NMR studies indicate (1) is asymmetric about the C2 axis in contra
st to what has been previously reported. Little, if any, enhancement of lum
inescence was observed with Zn, Cd, Ru or Eu treated DFO developed latent f
ingerprints. This lack of enhancement was also borne out by solution lumine
scence studies. Given this lack of enhancement of luminescence, solutions o
f (I) and the four metal ions above were analyzed by electrospray mass spec
trometry (ESMS). This indicated the formation of predominantly 1:1 complexe
s of (1) with both Zn and Cd, and the 2:1 complex with ruthenium. No eviden
ce of a Eu complex was found by ESMS. (C) 2001 Elsevier Science Ireland Ltd
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