Fluorescence Quenching of Benzaldehyde in Water by Hydrogen Atom Abstraction

Fletcher, Katharyn M.; Bunz, Uwe H. F.; Dreuw, Andreas

doi:10.1002/cphc.201501059

Cited by 7 publications

(4 citation statements)

References 41 publications

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“…Until recently, the quenching of the fluorescence of excited benzaldehyde ( 9) was unreasonably thought to originate from the basicity of the aldehyde. A recent publication though came to empower the statement that the HAT properties of benzaldehyde (8) are responsible for the observed quenching of the fluorescence [34].…”

Section: Review Photophysical Properties Of Carbonyl Compoundsmentioning

confidence: 99%

Aldehydes as powerful initiators for photochemical transformations

Θεοδωροπούλου

Nikitas

Kokotos

2020

Beilstein J. Org. Chem.

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Photochemistry, the use of light to promote organic transformations, has been known for more than a century but only recently has revolutionized the way modern chemists are thinking. Except from transition metal-based complexes, small organic molecules have been introduced as catalysts or initiators. In this review, we summarize the potential that (aromatic or aliphatic) aldehydes have as photoinitiators. The photophysical properties and photoreactivity of benzaldehyde are initially provided, followed by applications of aldehydes as initiators for polymerization reactions. Finally, the applications to date regarding aldehydes as photoinitiators in organic synthesis are presented.

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Section: Review Photophysical Properties Of Carbonyl Compoundsmentioning

confidence: 99%

Aldehydes as powerful initiators for photochemical transformations

Θεοδωροπούλου

Nikitas

Kokotos

2020

Beilstein J. Org. Chem.

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“…The water induced aggregation induced emission is one such example, [1][2][3] but water also quench emission. [9,10] Due to directional properties associated with hydrogen bonds and abilities of different functional groups to bind to a substrate, such effects influence the aggregation patterns of a fluorophore to cause or inhibit AIE. [5] It is also well known that non-covalently linked selfassemblies of fluorescent oxime molecules have interesting optical properties.…”

Section: Introductionmentioning

confidence: 99%

“…It may so happen that despite the parent compound showing conventional emission under ambient conditions, it may show AIE under confined media. The water induced aggregation induced emission is one such example, but water also quench emission ,. Due to directional properties associated with hydrogen bonds and abilities of different functional groups to bind to a substrate, such effects influence the aggregation patterns of a fluorophore to cause or inhibit AIE …”

Section: Introductionmentioning

confidence: 99%

Water‐Assisted Emission Enhancement of 2‐Hydroxynaphthaldoxime and Related Compounds

Tarai

Baruah

2018

ChemistrySelect

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The combined contributions from the excited‐state intramolecular proton‐transfer and aggregation‐induced emission in the photoluminescence of compounds namely 2‐hydroxynaphthaldoxime, 2‐methoxynaphthaldoxime, 2‐hydroxynaphthaldehyde and 1‐[(methylimino)methyl]naphthalen‐2‐ol were established. For such a purpose the changes in the fluorescence emission of these compounds in different solvents upon addition of water and from the fluorescence emission life‐time decay profiles were studied. 1H‐NMR titration of the 2‐hydroxynaphthaldoxime with D2O had provided clear evidence on the role of water molecules to disrupt the C−H⋅⋅⋅O interactions in assembly of 2‐hydroxynaphthaldoxime to orient the aromatic naphthalene rings differently to enhance the fluorescence emissions. Dynamic light scattering studies and scanning electron micrographs had showed that there were differences between the types of aggregation present in solid state and in solution. In solution the average size of the aggregates of 2‐hydroxynaphthaldoxime were increased upon addition of water. 2‐Hydroxynaphthaldoxime formed well defined cocrystal with tetrabutylammonium chloride but the tetrabutylammonium hydroxide formed salt of 2‐hydroxynaphthaldoxime by deprotonating hydroxy‐group. Accordingly the fluorescence emission changes of 2‐hydroxynaphthaldoxime caused by tetrabutylammonium hydroxide was different from the emission showed by the cocrystal with tetrabutylammonium chloride.

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“…The PL intensity ratios increased until they exceeded 100% after 24 h of baking at 150 °C. The weaker PL before baking can be attributed to the interaction between the absorbed water molecules and the PD chromophores within the LDH, which is possible according to theoretical and experimental investigations on some compounds with fluorescent chromophores , . This interaction may also be caused by the formation of localized electronic surface states, minimizing the optimum FL capabilities of PD.…”

Section: Resultsmentioning

confidence: 99%

Achieving Solidification and Redispersion of Semiconducting Polymer Dots by Layered Double Hydroxide Incorporation

Liu

Wang

Chen

et al. 2017

ACS Appl. Nano Mater.

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Solidification and aqueous redispersion of fluorophores are characteristically challenging because of aggregation quenching and random shifts of emission. Carbon-based polymer dots (PDs) have recently shown photoluminescent (PL) performances superior to those of conventional dyes and inorganic quantum dots (QDs) but suffer from significant fluorescence (FL) quenching and irreversible aqueous dispersion after solidification, which limits their applications in practical biomedicine and optical devices. In this work, we have compared three strategies by utilizing layered double hydroxides (LDHs) to effectively solidify PDs as robust and redispersible composites with well-preserved high brightness against wide pH (pH = 4−12) and strong ionic strength conditions, more stable than the pristine PDs. The resulting PD−LDH nanocomposites also show in vitro/in vivo bioimaging ability with low cytotoxicity and improved photostability. In addition, these composites exhibit high thermal stability at 150 °C for at least 96 h. The composites produced by a one-step physical mixing approach (∼10 min) of LDHs and PDs (p-PLDH) exhibited PL performances comparable to those of the conventional multistep composites (m-PLDH), which require tremendous effort (at least 7 days) to prepare. Structural studies further revealed that the deshaping behavior of PDs and the interflake sandwich assembly of LDHs contributed to the robust FL properties. Because of the simple synthesis, durable photostability, high aqueous redispersion, and multicolor emissions (ranging from blue to near-IR) of these PD−LDH nanocomposites, we believe that they are promising candidates for advanced biorelated technologies and optoelectronics.

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Fluorescence Quenching of Benzaldehyde in Water by Hydrogen Atom Abstraction

Cited by 7 publications

References 41 publications

Aldehydes as powerful initiators for photochemical transformations

Aldehydes as powerful initiators for photochemical transformations

Water‐Assisted Emission Enhancement of 2‐Hydroxynaphthaldoxime and Related Compounds

Achieving Solidification and Redispersion of Semiconducting Polymer Dots by Layered Double Hydroxide Incorporation

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