Cooperative Effect of Spacer and Lewis Base on Highly Reversible Spectral Changes of the Octaethylporphyrin Chromatic System in Sensitivity, Stability, and Visibility to Trifluoroacetic Acid

Abstract

The diacetylene-group connected chromatic system of [octaethylporphyrin]-[spacer]-[Lewis base] triads (OEP-SPC-LB) was conclusively studied, in which a trigger-like interaction of the terminal LB with trifluoroacetic acid (TFA) dramatically affects the inherent electronic properties of OEP. The 1H NMR, IR, and electronic absorption spectral properties of these OEP derivatives were examined, and were contemplated in view of a cooperative effect of SPC and LB on their OEP nucleus. Based on the results from this study, the structural elements for molecular design will be proposed in order to improve their reversible spectral changes between neutral and acidic media in terms of sensitivity, stability, and visibility to TFA.

Synthesis and reactivity of 9,10-bis(4-trimethylsilylethynylbuta-1,3-diynyl)anthracene derived chromophores

“…4 Connecting two nickel octaethylporphyrins (OEP) with the bis(butadiynyl)anthracene spacer was shown to result in exceptionally high electronic communication between the two OEP termini. 5…”

Materials Nanoarchitectonics for Mechanical Tools in Chemical and Biological Sensing

“…The designed and synthesized molecules are examined by using spectral methods, such as NMR‐spectroscopy‐based chiral discrimination, fluorescence‐based ion/molecular detection, and other optical‐based methods . These approaches can be regarded as chemistry‐based tools.…”

“…[9] The designed and synthesized molecules are examined by using spectralm ethods, such as NMR-spectroscopy-based chiral discrimination, [10] fluorescence-based ion/molecular detection, [11] and other optical-based methods. [12] These approaches can be regarded as chemistry-based tools. In many cases, these molecular and supramolecular sensings ystems are coupled with variousd evice-based tools, such as electrodes, transistors, and advanced nanotechnology devices.…”