Cyclopenta[b]naphthalene cyanoacrylate dyes: Synthesis and evaluation as fluorescent molecular rotors
| Autor: | Emmanuel A. Theodorakis, Kristyna M. Elbel, Kay M. Brummond, Billie A. Hardigree, Laura S. Kocsis, Mark A. Haidekker |
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| Jazyk: | angličtina |
| Rok vydání: | 2015 |
| Předmět: |
Quantum yield
Conjugated system Naphthalenes Photochemistry Biochemistry Article Fluorescence Medicinal and Biomolecular Chemistry Bathochromic shift Cyanoacrylates Physical and Theoretical Chemistry Fluorescent Dyes Cycloaddition Reaction Molecular Structure Spectrometry Chemistry Viscosity Organic Chemistry Solvatochromism Acceptor Spectrometry Fluorescence Intramolecular force Excited state Drug Design Solvents |
| Zdroj: | Kocsis, LS; Elbel, KM; Hardigree, BA; Brummond, KM; Haidekker, MA; & Theodorakis, EA. (2015). Cyclopenta[b]naphthalene cyanoacrylate dyes: Synthesis and evaluation as fluorescent molecular rotors. Organic and Biomolecular Chemistry, 13(10), 2965-2973. doi: 10.1039/c4ob02563f. UC San Diego: Retrieved from: http://www.escholarship.org/uc/item/7gs2m6s1 Organic & biomolecular chemistry, vol 13, iss 10 |
| DOI: | 10.1039/c4ob02563f. |
| Popis: | © 2015 The Royal Society of Chemistry. We describe the design, synthesis and fluorescent profile of a family of environment-sensitive dyes in which a dimethylamino (donor) group is conjugated to a cyanoacrylate (acceptor) unit via a cyclopenta[b]naphthalene ring system. This assembly satisfies the typical D-π-A motif of a fluorescent molecular rotor and exhibits solvatochromic and viscosity-sensitive fluorescence emission. The central naphthalene ring system of these dyes was synthesized via a novel intramolecular dehydrogenative dehydro-Diels-Alder (IDDDA) reaction that permits incorporation of the donor and acceptor groups in variable positions around the aromatic core. A bathochromic shift of excitation and emission peaks was observed with increasing solvent polarity but the dyes exhibited a complex emission pattern with a second red emission band when dissolved in nonpolar solvents. Consistent with other known molecular rotors, the emission intensity increased with increasing viscosity. Interestingly, closer spatial proximity between the donor and the acceptor groups led to decreased viscosity sensitivity combined with an increased quantum yield. This observation indicates that structural hindrance of intramolecular rotation dominates when the donor and acceptor groups are in close proximity. The examined compounds give insight into how excited state intramolecular rotation can be influenced by both the solvent and the chemical structure. This journal is |
| Databáze: | OpenAIRE |
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