Zhou, Ping; Aschauer, Ulrich; Decurtins, Silvio; Feurer, Thomas; Häner, Robert; Liu, Shi-Xia (2023). Merging of Azulene and Perylene Diimide for Optical pH Sensors. Molecules, 28(18), p. 6694. MDPI 10.3390/molecules28186694
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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, and UV-visible absorption spectroscopy. Direct comparison of their electronic properties leads us to the conclusion that a significant change in the localization of HOMO and LUMO occurs upon the fusion of azulene and perylene diimide in 2, leading to the lack of intramolecular charge-transfer character for transitions in the visible spectral region. Density functional theory (DFT) and time-dependent DFT (TD-DFT) calculations were performed to gain further insight into various electronic transitions. Moreover, 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. Our findings pave the way for manipulating the relative HOMO and LUMO energy levels of organic chromophores by fusing non-alternant azulenes to an otherwise flat PAH, which could possibly lead to applications in organic electronics and optical sensors.
Item Type: |
Journal Article (Original Article) |
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Division/Institute: |
08 Faculty of Science > Institute of Applied Physics 08 Faculty of Science > Institute of Applied Physics > Lasers 08 Faculty of Science > Department of Chemistry, Biochemistry and Pharmaceutical Sciences (DCBP) |
UniBE Contributor: |
Zhou, Ping, Decurtins, Silvio, Feurer, Thomas, Häner, Robert, Liu, Shi-Xia |
Subjects: |
500 Science > 570 Life sciences; biology 500 Science > 540 Chemistry 600 Technology > 620 Engineering |
ISSN: |
1420-3049 |
Publisher: |
MDPI |
Language: |
English |
Submitter: |
Silvio Decurtins |
Date Deposited: |
21 Sep 2023 09:10 |
Last Modified: |
07 Aug 2024 15:45 |
Publisher DOI: |
10.3390/molecules28186694 |
BORIS DOI: |
10.48350/186395 |
URI: |
https://boris.unibe.ch/id/eprint/186395 |
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