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

ChemistryOpen

Dr. Loredana Leone³  Dr. Alessandro Pezzella³  Prof. Orlando Crescenzi³  Prof. Alessandra Napolitano²  Prof. Vincenzo Barone¹ 

[1] Scuola Normale Superiore, Pisa, Italy;E-mail address: 关键词: acidichromism;    aldehydes;    benzothiazine;    cryptography;    cyanine dyes;   

DOI  :  10.1002/open.201402164

来源: Wiley

【 摘 要 】

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.

【 授权许可】

CC BY-NC-ND   
© 2014 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA.

Creative Commons Attribution-NonCommercial-NoDerivs License, which permits use and distribution in any medium, provided the original work is properly cited, the use is non-commercial and no modifications or adaptations are made.