Advances in Fingerprint Technology.pdf

Figure 5.15 1,2-Indanedione (III) and some of its analogues that give fluorogenic
reaction with amino acids and with latent fingerprints: III, 1,2-indanedione; XXIV,
5,6-dimethoxyindanedione; XXV, 6-methoxy-1,2-indanedione (and other isomers);
XXVI, 6-hydroxy-1,2-indanedione (and other isomers). (From Hauze, D.B., Petrovskaia,
O.G., Taylor, B., Joullié, M.M., Ramotowski, R., and Cantu, A.A., J.
Forensic Sci., 43, 744, 1998; Wiesner, S., Optimization of the Indanedione Process
for Fingerprint Development, M.Sc. thesis, Casali Institute of Applied Chemistry,
The Hebrew University of Jerusalem, Israel, 2001.)
1,2-Indanedione
The most recent, remarkable discovery in this field is 1,2-indanedione. To
develop new routes to ninhydrin analogues, Joullié, Cantu, and co-workers
synthesized and evaluated another class of compounds closely related to
ninhydrin: 1,2-indanediones (Figure 5.15). These compounds were prepared
and described in the chemical literature prior to Joullié, but never before had
they been examined as potential amino acid or fingerprint reagents.
Methanolic solutions of various 1,2-indanediones were applied to amino
acid spots on filter paper. They afforded light pink stains that fluoresce
brightly upon illumination with green light. 144,145 Secondary treatment with
zinc nitrate increased the fluorescence dramatically, particularly when
5,6-dimethoxy-1,2-indanedione (XXIV, Figure 5.15) was used as a reagent.
The fluorescence is stronger than with DFO-treated stains. Heat and humidity
also have an augmentative effect on the fluorescence, but cooling to liquid
nitrogen temperature is unnecessary.
Initial experiments with latent fingerprints under similar conditions
afforded brightly fluorescing fingerprint images. 145
The effects of further structural modifications in the indanedione series
were studied by Almog et al.; in their opinion, 1,2-indanedione itself, even
without secondary treatment, is at least as sensitive as DFO. 146 They also
devised a novel synthetic route to some indanediones147 that could not be
prepared by the original method developed by Cava et al. 148
The first positive experiments with indanediones were carried out in
methanolic solutions. Nevertheless, Petrovskaia and Joullié, 112 Wilkinson, 149
and Wiesner et al. 150 recommend the use of indanedione in alcohol-free
carriers because alcohols (methanol, ethanol, isopropanol) reduce the effectiveness
of the reagent due to the formation of hemiketals. Roux et al., however,