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Trichocyanines: a Red-Hair-Inspired Modular Platform for Dye-Based One-Time-Pad Molecular Cryptography.

Leone L, Pezzella A, Crescenzi O, Napolitano A, Barone V, d'Ischia M - ChemistryOpen (2015)

Bottom Line: These novel acidichromic cyanine-type dyes inspired by red hair pigments were synthesized and characterized with the aid of density functional theory (DFT) calculations.This versatile dye platform can generate an expandable palette of colors and appears to be specifically suited to implement an unprecedented single-use asymmetric molecular cryptography system.With this system, we intend to pioneer the translation of digital public-key cryptography into a chemical-coding one-time-pad-like system.

View Article: PubMed Central - PubMed

Affiliation: Department of Chemical Sciences, University of Naples Federico II Via Cintia 4, 80126, Naples, Italy.

ABSTRACT
Current molecular cryptography (MoCryp) systems are almost exclusively based on DNA chemistry and reports of cryptography technologies based on other less complex chemical systems are lacking. We describe herein, as proof of concept, the prototype of the first asymmetric MoCryp system, based on an 8-compound set of a novel bioinspired class of cyanine-type dyes called trichocyanines. These novel acidichromic cyanine-type dyes inspired by red hair pigments were synthesized and characterized with the aid of density functional theory (DFT) calculations. Trichocyanines consist of a modular scaffold easily accessible via an expedient condensation of 3-phenyl- or 3-methyl-2H-1,4-benzothiazines with N-dimethyl- or o-methoxyhydroxy-substituted benzaldehyde or cinnamaldehyde derivatives. The eight representative members synthesized herein can be classified as belonging to two three-state systems tunable through four different control points. This versatile dye platform can generate an expandable palette of colors and appears to be specifically suited to implement an unprecedented single-use asymmetric molecular cryptography system. With this system, we intend to pioneer the translation of digital public-key cryptography into a chemical-coding one-time-pad-like system.

No MeSH data available.


Related in: MedlinePlus

Summary of the main control points for the new red-hair-inspired dye platform.
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fig07: Summary of the main control points for the new red-hair-inspired dye platform.

Mentions: All compounds exhibited good resistance to fatigue over several cycles of pH switching (Figure 6). From the above data, we can conclude that the new cyanine-type scaffold displays four distinct control points for property tailoring and tuning: 1) the proton sensitive benzothiazine imine center, allowing for absorption shift and/or for complementary color/emission switch, 2) the 3-substituent on the benzothiazine ring, controlling emission, 3) the length of the π bridge, which finely tunes electronic communication between the push-pull structural elements, and 4) the electron-donating substituent(s) on the phenyl ring (Figure 7).


Trichocyanines: a Red-Hair-Inspired Modular Platform for Dye-Based One-Time-Pad Molecular Cryptography.

Leone L, Pezzella A, Crescenzi O, Napolitano A, Barone V, d'Ischia M - ChemistryOpen (2015)

Summary of the main control points for the new red-hair-inspired dye platform.
© Copyright Policy - open-access
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC4522187&req=5

fig07: Summary of the main control points for the new red-hair-inspired dye platform.
Mentions: All compounds exhibited good resistance to fatigue over several cycles of pH switching (Figure 6). From the above data, we can conclude that the new cyanine-type scaffold displays four distinct control points for property tailoring and tuning: 1) the proton sensitive benzothiazine imine center, allowing for absorption shift and/or for complementary color/emission switch, 2) the 3-substituent on the benzothiazine ring, controlling emission, 3) the length of the π bridge, which finely tunes electronic communication between the push-pull structural elements, and 4) the electron-donating substituent(s) on the phenyl ring (Figure 7).

Bottom Line: These novel acidichromic cyanine-type dyes inspired by red hair pigments were synthesized and characterized with the aid of density functional theory (DFT) calculations.This versatile dye platform can generate an expandable palette of colors and appears to be specifically suited to implement an unprecedented single-use asymmetric molecular cryptography system.With this system, we intend to pioneer the translation of digital public-key cryptography into a chemical-coding one-time-pad-like system.

View Article: PubMed Central - PubMed

Affiliation: Department of Chemical Sciences, University of Naples Federico II Via Cintia 4, 80126, Naples, Italy.

ABSTRACT
Current molecular cryptography (MoCryp) systems are almost exclusively based on DNA chemistry and reports of cryptography technologies based on other less complex chemical systems are lacking. We describe herein, as proof of concept, the prototype of the first asymmetric MoCryp system, based on an 8-compound set of a novel bioinspired class of cyanine-type dyes called trichocyanines. These novel acidichromic cyanine-type dyes inspired by red hair pigments were synthesized and characterized with the aid of density functional theory (DFT) calculations. Trichocyanines consist of a modular scaffold easily accessible via an expedient condensation of 3-phenyl- or 3-methyl-2H-1,4-benzothiazines with N-dimethyl- or o-methoxyhydroxy-substituted benzaldehyde or cinnamaldehyde derivatives. The eight representative members synthesized herein can be classified as belonging to two three-state systems tunable through four different control points. This versatile dye platform can generate an expandable palette of colors and appears to be specifically suited to implement an unprecedented single-use asymmetric molecular cryptography system. With this system, we intend to pioneer the translation of digital public-key cryptography into a chemical-coding one-time-pad-like system.

No MeSH data available.


Related in: MedlinePlus