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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

Writing with trichocyanines generated in situ. Left: the control shows filter paper strips dipped into three different aldehyde solutions in methanolic p-toluenesulfonic acid (top: 4-dimethylaminocinnamaldehyde, middle: ferulic aldehyde, bottom: 4-dimethylaminobenzaldehyde). Middle: image taken immediately after writing on the stripes with a methanol solution of 3-phenyl-2H-1,4-benzothiazine. Right: image 3 min after writing.
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fig09: Writing with trichocyanines generated in situ. Left: the control shows filter paper strips dipped into three different aldehyde solutions in methanolic p-toluenesulfonic acid (top: 4-dimethylaminocinnamaldehyde, middle: ferulic aldehyde, bottom: 4-dimethylaminobenzaldehyde). Middle: image taken immediately after writing on the stripes with a methanol solution of 3-phenyl-2H-1,4-benzothiazine. Right: image 3 min after writing.

Mentions: Use of a CMS instead of a conventional digital writing system imparts robustness against breaches, because it requires shipment of very complex strings of chemical compounds. Efficient intrusion detection is based on the simple fact that information decryption requires access to the objects (the chemical mixtures), and any intrusion would be immediately apparent by the failure to receive the chemical code. Notably, the fast and efficient acid-promoted condensation chemistry used for trichocyanine synthesis may be suitable for chemical coding via inkjet printing. In addition, it is possible to generate trichocyanines directly on a solid support such as paper (Figure 9). This would allow the use of two collections of single-use cartridges as the generating sets, making both direct duplication of the mixtures and chemical analysis of printed strings a virtually impossible event to any expert chemist who wishes to crack the code.


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)

Writing with trichocyanines generated in situ. Left: the control shows filter paper strips dipped into three different aldehyde solutions in methanolic p-toluenesulfonic acid (top: 4-dimethylaminocinnamaldehyde, middle: ferulic aldehyde, bottom: 4-dimethylaminobenzaldehyde). Middle: image taken immediately after writing on the stripes with a methanol solution of 3-phenyl-2H-1,4-benzothiazine. Right: image 3 min after writing.
© Copyright Policy - open-access
Related In: Results  -  Collection

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

fig09: Writing with trichocyanines generated in situ. Left: the control shows filter paper strips dipped into three different aldehyde solutions in methanolic p-toluenesulfonic acid (top: 4-dimethylaminocinnamaldehyde, middle: ferulic aldehyde, bottom: 4-dimethylaminobenzaldehyde). Middle: image taken immediately after writing on the stripes with a methanol solution of 3-phenyl-2H-1,4-benzothiazine. Right: image 3 min after writing.
Mentions: Use of a CMS instead of a conventional digital writing system imparts robustness against breaches, because it requires shipment of very complex strings of chemical compounds. Efficient intrusion detection is based on the simple fact that information decryption requires access to the objects (the chemical mixtures), and any intrusion would be immediately apparent by the failure to receive the chemical code. Notably, the fast and efficient acid-promoted condensation chemistry used for trichocyanine synthesis may be suitable for chemical coding via inkjet printing. In addition, it is possible to generate trichocyanines directly on a solid support such as paper (Figure 9). This would allow the use of two collections of single-use cartridges as the generating sets, making both direct duplication of the mixtures and chemical analysis of printed strings a virtually impossible event to any expert chemist who wishes to crack the code.

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