Picking Out Logic Operations in a Naphthalene β‐Diketone Derivative by Using Molecular Encapsulation, Controlled Protonation, and DNA Binding

ChemistryOpen

Sameena Yousuf⁴  Ritty Alex⁴  Paulraj Mosae Selvakumar³  Dr. Israel V. M. V. Enoch¹  Dr. Palani Sivagnana Subramanian² 

[1] E-mail address: E-mail address: 关键词: β-cyclodextrin;    fluorescence spectroscopy;    host—guest interaction;    molecular logic gates;    naphthalene;    supramolecular chemistry;   

DOI  :  10.1002/open.201500034

来源: Wiley

【 摘 要 】

Abstract

On–off switching and molecular logic in fluorescent molecules are associated with what chemical inputs can do to the structure and dynamics of these molecules. Herein, we report the structure of a naphthalene derivative, the fashion of its binding to β-cyclodextrin and DNA, and the operation of logic possible using protons, cyclodextrin, and DNA as chemical inputs. The compound crystallizes out in a keto-amine form, with intramolecular N−H⋅⋅⋅O bonding. It shows stepwise formation of 1:1 and 1:2 inclusion complexes with β-cyclodextrin. The aminopentenone substituents are encapsulated by β-cyclodextrin, leaving out the naphthalene rings free. The binding constant of the β-cyclodextrin complex is 512 m⁻¹. The pK_a value of the guest molecule is not greatly affected by the complexation. Dual input logic operations, based on various chemical inputs, lead to the possibility of several molecular logic gates, namely NOR, XOR, NAND, and Buffer. Such chemical inputs on the naphthalene derivative are examples of how variable signal outputs based on binding can be derived, which, in turn, are dependent on the size and shape of the molecule.

【 授权许可】

CC BY-NC-ND   
© 2015 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA.

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