Article
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Merging of Azulene and Perylene Diimide for Optical pH Sensors
Version 1
: Received: 24 August 2023 / Approved: 24 August 2023 / Online: 24 August 2023 (13:27:09 CEST)
A peer-reviewed article of this Preprint also exists.
Zhou, P.; Aschauer, U.; Decurtins, S.; Feurer, T.; Häner, R.; Liu, S.-X. Merging of Azulene and Perylene Diimide for Optical pH Sensors. Molecules 2023, 28, 6694. Zhou, P.; Aschauer, U.; Decurtins, S.; Feurer, T.; Häner, R.; Liu, S.-X. Merging of Azulene and Perylene Diimide for Optical pH Sensors. Molecules 2023, 28, 6694.
Abstract
Polycyclic aromatic hydrocarbons (PAHs) have emerged as promising materials for organic electronics, including organic photovoltaics (OPVs), organic field-effect transistors (OFETs), and organic light-emitting diodes (OLEDs). Particularly, non-hexagonal ring-fused PAHs are highly desirable due to their unique optoelectronic properties. Herein, a new redox-active azulene-perylene diimide triad 1 and its ring-fused counterpart, diazulenocoronene diimide 2, were synthesized and fully characterized by a combination of NMR, cyclic voltammetry, spectroelectrochemistry, and UV-visible absorption spectroscopy. Density functional theory (DFT) and time-dependent DFT (TD-DFT) calculations were performed to gain further insight into various electronic transitions. Interestingly, we found that the adaptive response to acids and bases manifests itself in a reversible two-color-change that can be attributed to changes in the chemical structures.
Keywords
Azulene; Cyclic voltammetry; Computational chemistry; Optoelectronic properties; Intramolecular charge transfer; Perylene diimide; Polycyclic aromatic hydrocarbons; Ring-fused system; Chemical sensors
Subject
Chemistry and Materials Science, Physical Chemistry
Copyright: This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
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