Journal Article

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

Selvakumar, Paulraj Mosae, Sun, Yu, Yousuf, Sameena, Alex, Ritty, Subramanian, Palani Sivagnana, Enoch, Israel V. M. V.

2015

Overview

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 pKa 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. Lifting logic from molecules: Compounds or complexes that have different properties depending on specific inputs, e.g. pH, can be used to generate Boolean logic functions. Naphthalene β‐diketone derivatives bind to DNA and β‐cyclodextrin, where aminopentenone substituents are encapsulated inside the β‐cyclodextrin cavity. The resulting compound displays NOR, XOR, NAND, and Buffer logic operations based on proton, cyclodextrin, and DNA as chemical inputs.

• Publisher: John Wiley & Sons, Inc,John Wiley & Sons, Ltd
• Subject: Binding / Cage molecules / Chemical bonds / Cyclodextrins / Deoxyribonucleic acid / Derivatives / Diketones / Encapsulation / Fluorescence / fluorescence spectroscopy / host—guest interaction / Inclusion complexes / Logic / Logic circuits / molecular logic gates / Molecular structure / Naphthalene / Protonation / supramolecular chemistry / β-cyclodextrin