ArticleACS omega2018
How Do Amides Affect the Electronic Properties of Pyrene?
Article in ACS omega, 2018. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 10 papers.
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Who cites it
10 citing papers in PubMed, 32 citations in OpenAlex.
- A Miniaturized Electrochemical SERS Chip with 3D Nanoporous Gold Interface for Qualitative and Quantitative Analysis of Organic Pollutants and their Oxidation Intermediates.Small (Weinheim an der Bergstrasse, Germany) · 2025Article
- Dipoles affect conformational equilibrium.Journal of photochemistry and photobiology. A, Chemistry · 2025Article
- Twisting, Hydrogen Bonding, Exciplex Formation, and Charge Transfer. What Makes a Bright Fluorophore Not So Bright?The Journal of organic chemistry · 2025Article
- Tuning the Activity of 1,5-Diamino-naphthalene Through an Asymmetric Mono-Amidation with Pyroglutamic Acid.Molecules (Basel, Switzerland) · 2025Article
- Article
- How Permanent Are the Permanent Macrodipoles of Anthranilamide Bioinspired Molecular Electrets?Journal of the American Chemical Society · 2024Article
- The magic of biaryl linkers: the electronic coupling through them defines the propensity for excited-state symmetry breaking in quadrupolar acceptor-donor-acceptor fluorophores.Chemical science · 2023Article
- Making Nitronaphthalene Fluoresce.The journal of physical chemistry letters · 2021Article
- How does tautomerization affect the excited-state dynamics of an amino acid-derivatized corrole?Photosynthesis research · 2021Article
- Multifaceted aspects of charge transfer.Physical chemistry chemical physics : PCCP · 2020Article
Corrections and comments
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Authors and funding
7 authors at 2 institutions in 2 countries.
Funding
No grant is acknowledged in the PubMed record.
Abstract
The electronic properties of amide linkers, which are intricate components of biomolecules, offer a wealth of unexplored possibilities. Herein, we demonstrate how the different modes of attaching an amide to a pyrene chromophore affect the electrochemical and optical properties of the chromophore. Thus, although they cause minimal spectral shifts, amide substituents can improve either the electron-accepting or electron-donating capabilities of pyrene. Specifically, inversion of the amide orientation shifts the reduction potentials by 200 mV. These trends indicate that, although amides affect to a similar extent the energies of the ground and singlet excited states of pyrene, the effects on the doublet states of its radical ions are distinctly different. This behavior reflects the unusually strong orientation dependence of the resonance effects of amide substituents, which should extend to amide substituents on other types of chromophores in general. These results represent an example where the Hammett sigma constants fail to predict substituent effects on electrochemical properties. On the other hand, Swain-Lupton parameters are found to be in good agreement with the observed trends. Examination of the frontier orbitals of the pyrene derivatives and their components reveals the underlying reason for the observed amide effects on the electronic properties of this polycyclic aromatic hydrocarbon and points to key molecular-design strategies for electronic and energy-conversion systems.
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Registered trials
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