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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

Structures of trichochromes isolated from red human hair and avian feathers.
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fig01: Structures of trichochromes isolated from red human hair and avian feathers.

Mentions: An attractive source of inspiration for innovative cyanine-type systems suitable for MoCryp applications came from the peculiar photochromic and acidichromic properties of Δ2,2′-bi(benzothiazine)-based chromophores21–23 modeled after pheomelanin pigments in red human hair and in feathers (Figure 1).24–26 The most characteristic feature of these compounds is their doubly cross-conjugated yellow-to-red chromophore which undergoes a marked bathochromic shift to an intense blue coloration after exposure to acids.22,23


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)

Structures of trichochromes isolated from red human hair and avian feathers.
© Copyright Policy - open-access
Related In: Results  -  Collection

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

fig01: Structures of trichochromes isolated from red human hair and avian feathers.
Mentions: An attractive source of inspiration for innovative cyanine-type systems suitable for MoCryp applications came from the peculiar photochromic and acidichromic properties of Δ2,2′-bi(benzothiazine)-based chromophores21–23 modeled after pheomelanin pigments in red human hair and in feathers (Figure 1).24–26 The most characteristic feature of these compounds is their doubly cross-conjugated yellow-to-red chromophore which undergoes a marked bathochromic shift to an intense blue coloration after exposure to acids.22,23

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