Theoretical study of m-dansylaminophenylboronic acid and their species: A sugar chemosensor

Crespo‐Otero, Rachel; Suardíaz, Reynier; Pina‐Luis, Georgina; Valdés, Mayra Granda; Dı́az-Garcı́a, Marta Elena; Montero, Luis A.

doi:10.1016/j.theochem.2007.12.028

Cited by 2 publications

(2 citation statements)

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“…In some studies, probe-solvent or analyte-solvent interactions have been investigated by including a few discrete solvent molecules. 87 Furthermore, a hybrid quantum mechanics/molecular mechanics (QM/MM) approach has also been used to describe probe-analyte-solvent systems, 43,79,88 whereby the probe or probe-analyte complex is treated by QM and the solvent is treated by MM.…”

Section: Tddft Calculationsmentioning

confidence: 99%

The sensing mechanism studies of the fluorescent probes with electronically excited state calculations

Han

2017

WIREs Comput Mol Sci

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Recent research has indicated that fluorescent probes have tremendous potential for the selective detection of chemical and biological species. Over the past decade, researchers have proposed a series of fluorescence‐based sensing mechanisms of such probes by the calculation of their electronic excited states. Investigations of sensing mechanisms have been based on deep insights into the interactions between probe molecules and their target species, as well as their fluorescence properties. Advances in calculation methods, modeling software, and computational power have enabled researchers to use excited‐state theoretical calculations to reproduce experimental fluorescence phenomena and then provide molecular‐level explanations thereof. In this advanced review, we describe the evolution of theoretical studies on excited‐state sensing mechanisms for fluorescent probes that respond to target species. Focusing on calculation methods that facilitate investigation of the photophysical properties and excited‐state dynamics of probes, we emphasize sensing mechanisms mainly reported by our group. Most of these studies have been supported by theoretical predictions based on time‐dependent density functional theory. For this most popular excited‐state calculation method, vertical excitation energy, excited‐state geometrical optimization and a scan of the excited‐state potential energy surface should be noted in the calculation of electronic and molecular differences between the excited‐state probe and its reaction product with the target analyte. These state‐of‐the‐art calculations are of great importance for unraveling details of fluorescence‐based sensing mechanisms, including photochemical reactions (such as twist intramolecular charge transfer and excited‐state proton transfer) and excited‐state electronic processes (such as intramolecular charge transfer and photoinduced electron transfer). These studies have generated new and inspirational mechanistic proposals and have provided a systematic approach for the development of efficient fluorescent sensors. WIREs Comput Mol Sci 2018, 8:e1351. doi: 10.1002/wcms.1351 This article is categorized under: Structure and Mechanism > Computational Biochemistry and Biophysics Theoretical and Physical Chemistry > Spectroscopy

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Section: Tddft Calculationsmentioning

confidence: 99%

The sensing mechanism studies of the fluorescent probes with electronically excited state calculations

Han

2017

WIREs Comput Mol Sci

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“…Therefore, considerable efforts have been made to develop selective and sensitive fluorescent sensors for metal ions. In fact, we are involved in the development of abiotic receptors designed on the basis of the photoinduced electron transfer (PET) process. − A simplified picture of this process is the donor−acceptor (D−L−A) system (Scheme ). The donor group is covalently bound, through a rigid or flexible linker unit, to the acceptor.…”

Section: Introductionmentioning

confidence: 99%

Solid Phase Synthesis of N-Alkyl-bis-o-aminobenzamides for Metal Ion Sensing Based on a Fluorescent Dansyl Platform

2008

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In this paper, we report the synthesis on Merrifield's resin of alkyl-bis-o-aminobenzamides labeled with a fluorescent dansyl group for use in metal ion recognition. The influence of alkyl groups with different long chains (n = 1, 2, 4, 6) on the spectral fluorescence characteristics was studied. The sensing properties of the beads were evaluated by packing the resins into a flow-through cell for use in a FIA (flow injection analysis)format. Results demonstrated that for those materials with a longer alkyl chain, the fluorescence emission increased upon Li+, Na+, K+, Ca2+, and Mg2+ addition with a higher sensitivity for Mg2+. On the contrary,a fluorescence quenching was observed when Cu2+, Fe3+, or Zn2+ ions were added. The potential applicability of the sensing approach described in this paper for magnesium ions and the sensing response mechanism are outlined.

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Theoretical study of m-dansylaminophenylboronic acid and their species: A sugar chemosensor

Cited by 2 publications

References 5 publications

The sensing mechanism studies of the fluorescent probes with electronically excited state calculations

The sensing mechanism studies of the fluorescent probes with electronically excited state calculations

Solid Phase Synthesis of N-Alkyl-bis-o-aminobenzamides for Metal Ion Sensing Based on a Fluorescent Dansyl Platform

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