Excited-State Intramolecular Proton Transfer of the Natural Product Quercetin

Simkovitch, Ron; Huppert, Dan

doi:10.1021/acs.jpcb.5b04867

Cited by 38 publications

(37 citation statements)

References 43 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…In addition, the violet vertical lines stand for corresponding peak values obtained in the experiment. It has been found that the absorption peak assigned to the S 0 → S 1 transition process locates in 372 nm, which hasan amazingcoincidencethat the absorption wavelength isabout 380 nm in the experiment32. Following the photo-excitation process, quercein molecule will go through a fast radiative decay process from the S 1 state to the S 0 state, the fluorescence emission peak of normal construction at 434 nm is extremely close to the experimental value of 430 nm.…”

Section: Resultssupporting

confidence: 57%

“…However, the mechanism of the ESIPT processes is very elusive in the quercetin molecule32. Therefore, for further gaining the fluorescent emission and absorptionspectrum, wehave carriedout the theoretical calculation based on the quantum chemistry methods.…”

Section: Resultsmentioning

confidence: 99%

“…The two hydrogen bond groups existed in the quercetinstructureconsist of a common proton acceptor and twoproton donors in close proximity. The both proton donorsare thehydroxyl groupwhile the common proton acceptor is the carbonyl oxygen atom in the hydrogen bondgroup moiety32. In addition, two hydrogen bond groups form the five-membered and six-membered ring structure, respectively.…”

mentioning

confidence: 99%

“…Therefore, the interactions of hydrogenbond have been defined as the important driving force in the ESIPT process3536. Simkovitch et al have investigated the time-resolvedfluorescence of the quercetin experimentally throughthe steady-state absorption spectroscopy and fluorescent up-conversiontechniques32. However, the above measures cannotprimelyaccount for the two ESIPT processes that the proton jumps from the corresponding proton donor to the common proton acceptor.…”

mentioning

confidence: 99%

See 3 more Smart Citations

Theoretical Study of the ESIPT Process for a New Natural Product Quercetin

Yang

Zhao

2016

Sci Rep

View full text Add to dashboard Cite

The investigation of excited-state intramolecular proton transfer (ESIPT) has been carried out via the density functional theory (DFT) and the time-dependent density functional theory (TDDFT) method for natural product quercetin in dichloromethane (DCM) solvent. For distinguishing different types of intramolecular interaction, the reduced density gradient (RDG) function also has been used. In this study, we have clearly clarified the viewpoint that two kinds of tautomeric forms (K1, K2)originated from ESIPT processconsist inthe first electronic excited state (S1). The phenomenon of hydrogen bonding interaction strengtheninghas been proved by comparing the changes of infrared (IR) vibrational spectra and bond parameters of the hydrogen bonding groups in the ground state with that in the first excited state. The frontier molecular orbitals (MOs)provided visual electron density redistribution have further verified the hydrogen bond strengthening mechanism. It should be noted that the ESIPT process of the K2 form is easier to occur than that of the K1 form via observing the potential energy profiles. Furthermore, the RDG isosurfaces has indicated that hydrogen bonding interaction of the K2 form is stronger than that of the K1 formin the S1 state, which is also the reason why the ESIPT process of the K2 form is easier to occur.

show abstract

Section: Resultssupporting

confidence: 57%

Section: Resultsmentioning

confidence: 99%

mentioning

confidence: 99%

mentioning

confidence: 99%

See 2 more Smart Citations

Theoretical Study of the ESIPT Process for a New Natural Product Quercetin

Yang

Zhao

2016

Sci Rep

View full text Add to dashboard Cite

show abstract

“…Riedle and coworkers [5] reported a time constant of 30 fs for an ESIHT in HBT. [13,19] In a recent article, [20] we reported on a study of the ESIHT of quercetin in several solvents using the fluorescence upconversion technique with a 250 fs instrument-response function. [6] Recently, HBT was studied using a UV-pump IR probe by Nibbering, Batista, and coworkers.…”

Section: Introductionmentioning

confidence: 99%

Intramolecular Excited‐State Hydrogen Transfer in Rutin and Quercetin

Simkovitch

Huppert

2017

Israel Journal of Chemistry

Self Cite

View full text Add to dashboard Cite

Steady‐state and time‐resolved optical spectroscopy techniques were employed to study the excited‐state intramolecular hydrogen transfer (ESIHT) in rutin, a flavonol that contains a disaccharide and is a natural product in plants. The results are compared with those of a similar natural compound, quercetin, which also has a flavonol structure. The fluorescence decay signal of the normal form of these two compounds is composed of three time components. The ESIHT rate in both compounds has a time constant of 70 fs or less. The ESIHT processes of both compounds show a distinctive kinetic isotope effect of 1.5 or more. The intermediate and long‐time components are about 300 fs and a few picoseconds, respectively, for both compounds. The amplitude of the intermediate component in rutin is twice that of quercetin. We explain this difference as arising from the hydrogen bonding of the glucose in rutin to the ESIHT active site.

show abstract

Novel Quercetin Aggregation‐Induced Emission Luminogen (AIEgen) with Excited‐State Intramolecular Proton Transfer for In Vivo Bioimaging

Niu

Chen

et al. 2018

Adv Funct Materials

109

View full text Add to dashboard Cite

Aggregation‐induced emission luminogens (AIEgens) that undergo excited‐state intramolecular proton transfer (ESIPT) have many applications in bioimaging since they have high quantum efficiency in the aggregated state and a low background signal in aqueous solutions because of their large Stokes shift. One disadvantage of many of the AIEgens with ESIPT that has been described so far is that they require time‐consuming synthesis and the use of toxic reagents. Another disadvantage with most of these materials is that they are only used for bioimaging in cells and are unsuitable for in vivo bioimaging. Herein, a new AIEgen with ESIPT, quercetin (QC) is described, which is easily prepared from Sophora japonica. AIE is attributed to crystallization‐promoted keto emission. The fluorescence is temperature dependent and shows strong resistance to photobleaching. QC AIEgen with ESIPT is shown to have excellent biocompatibility and is successfully used for bioimaging both in cellular cytoplasm and in vivo.

show abstract

Excited-State Intramolecular Proton Transfer of the Natural Product Quercetin

Cited by 38 publications

References 43 publications

Theoretical Study of the ESIPT Process for a New Natural Product Quercetin

Theoretical Study of the ESIPT Process for a New Natural Product Quercetin

Intramolecular Excited‐State Hydrogen Transfer in Rutin and Quercetin

Novel Quercetin Aggregation‐Induced Emission Luminogen (AIEgen) with Excited‐State Intramolecular Proton Transfer for In Vivo Bioimaging

Contact Info

Product

Resources

About