ArticleMolecules (Basel, Switzerland)2019
Effect of the Substitution Position on the Electronic and Solvatochromic Properties of Isocyanoaminonaphthalene (ICAN) Fluorophores.
Article in Molecules (Basel, Switzerland), 2019. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 6 papers.
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Who cites it
6 citing papers in PubMed.
- Preparation and Optical Study of 1-Formamido-5-Isocyanonaphthalene, the Hydrolysis Product of the Potent Antifungal 1,5-Diisocyanonaphthalene.International journal of molecular sciences · 2023Article
- Synthesis and Photophysical Properties of α-(Molecules (Basel, Switzerland) · 2022Article
- Potential Original Drug for Aspergillosis: In Vitro and In Vivo Effects of 1-N,N-Dimethylamino-5-Isocyanonaphthalene (DIMICAN) onJournal of fungi (Basel, Switzerland) · 2022Article
- Isocyanonaphthol Derivatives: Excited-State Proton Transfer and Solvatochromic Properties.International journal of molecular sciences · 2022Article
- Optical Study of Solvatochromic Isocyanoaminoanthracene Dyes and 1,5-Diaminoanthracene.International journal of molecular sciences · 2022Article
- Antifungal Activity of an Original Amino-Isocyanonaphthalene (ICAN) Compound Family: Promising Broad Spectrum Antifungals.Molecules (Basel, Switzerland) · 2020Article
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Authors and funding
5 authors.
Funding
Abstract
The properties of 1,4-isocyanoaminonaphthalene (1,4-ICAN) and 2,6-isocyanoaminonaphthalene (2,6-ICAN) isomers are discussed in comparison with those of 1,5-isocyanoaminonaphthalene (1,5-ICAN), which exhibits a large positive solvatochromic shift similar to that of Prodan. In these isocyanoaminonaphthalene derivatives, the isocyano and the amine group serve as the donor and acceptor moieties, respectively. It was found that the positions of the donor and the acceptor groups in these naphthalene derivatives greatly influence the Stokes and solvatochromic shifts, which decrease in the following order: 1,5-ICAN > 2,6-ICAN > 1,4-ICAN. According to high-level quantum chemical calculations, this order is well correlated with the charge transfer character of these compounds upon excitation. Furthermore, unlike 1,5-ICAN, the 1,4-ICAN and 2,6-ICAN isomers showed relatively high quantum yields in water, that were determined to be 0.62 and 0.21, respectively. In addition, time-resolved fluorescence experiments revealed that both the radiative and non-radiative decay rates for these three ICAN isomers varied unusually with the solvent polarity parameter E
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