Fluorescent PET (photoinduced electron transfer) indicators for solvent polarity with quasi-step functional response

Bissell, Richard A.; Silva, A.Prasanna de; Thilak, W.; Fernando, M.L.; Patuwathavithana, Suram T.; Shantha, T.K.; Samarasinghe, Diyanath

doi:10.1016/s0040-4039(00)92645-5

Cited by 48 publications

(14 citation statements)

References 41 publications

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“…9,16,43 PET is also more favorable in polar solvents. 44 Kinetic aspects can play a significant role, in particular, PET becomes less effective with increasing distance between fluorophore and the PET group and an adverse nature and orientation of molecular orbitals may inhibit the process. 45−47 Nevertheless, these thermodynamic considerations generally enable a valuable estimation whether a PET process will take place and are suitable for identifying systems in which PET is impossible.…”

Section: Resultsmentioning

confidence: 99%

Enhancing Photoinduced Electron Transfer Efficiency of Fluorescent pH-Probes with Halogenated Phenols

et al. 2014

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Photoinduced electron transfer (PET), which causes pH-dependent quenching of fluorescent dyes, is more effectively introduced by phenolic groups than by amino groups which have been much more commonly used so far. That is demonstrated by fluorescence measurements involving several classes of fluorophores. Electrochemical measurements show that PET in several amino-modified dyes is thermodynamically favorable, even though it was not experimentally found, underlining the importance of kinetic aspects to the process. Consequently, the attachment of phenolic groups allows for fast and simple preparation of a wide selection of fluorescent pH-probes with tailor-made spectral properties, sensitive ranges, and individual advantages, so that a large number of applications can be realized. Fluorophores carrying phenolic groups may also be used for sensing analytes other than pH or molecular switching and signaling.

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Section: Resultsmentioning

confidence: 99%

Enhancing Photoinduced Electron Transfer Efficiency of Fluorescent pH-Probes with Halogenated Phenols

et al. 2014

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“…It should be mentioned here that the efficiency of a PET process can correlate with solvent polarity. For instance, for anthracence derivatives it was found to increase with polarity [ 56 ].…”

Section: Resultsmentioning

confidence: 99%

New fluorescent perylene bisimide indicators—a platform for broadband pH optodes

2011

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Asymmetric perylene bisimide (PBI) dyes are prepared and are shown to be suitable for the preparation of fluorescence chemosensors for pH. They carry one amino-functional substituent which introduces pH sensitivity via photoinduced electron transfer (PET) while the other one increases solubility. The luminescence quantum yields for the new indicators exceed 75% in the protonated form. The new indicators are non-covalently entrapped in polyurethane hydrogel D4 and poly(hydroxyalkylmethacrylates). Several PET functions including aliphatic and aromatic amino groups were successfully used to tune the dynamic range of the sensor. Because of their virtually identical spectral properties, various PBIs with selected PET functions can easily be integrated into a single sensor with enlarged dynamic range (over 4 pH units). PBIs with two different substitution patterns in the bay position are investigated and possess variable spectral properties. Compared with their tetrachloro analogues, tetra-tert-butyl-substituted PBIs yield more long-wave excitable sensors which feature excellent photostability. Cross-sensitivity to ionic strength was found to be negligible. The practical applicability of the sensors may be compromised by the long response times (especially in case of tetra-tert-butyl-substituted PBIs).Electronic supplementary materialThe online version of this article (doi:10.1007/s00216-010-4647-y) contains supplementary material, which is available to authorized users.

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“…2). The generally lower polarity of the bead surface environment when compared to the mixed aqueous medium has no significant effect on PET rates in our case,56,64,78–80 probably because of the rather exergonic PET process (as calculated for acetonitrile solution where Δ G PET = –0.3 eV). In other words, PET probably remains exergonic in the bead surface environment.…”

Section: Resultsmentioning

confidence: 56%

Population analysis to increase the robustness of molecular computational identification and its extension into the near-infrared for substantial numbers of small objects

et al. 2019

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Fluorescent PET (photoinduced electron transfer) indicators for solvent polarity with quasi-step functional response

Cited by 48 publications

References 41 publications

Enhancing Photoinduced Electron Transfer Efficiency of Fluorescent pH-Probes with Halogenated Phenols

Enhancing Photoinduced Electron Transfer Efficiency of Fluorescent pH-Probes with Halogenated Phenols

New fluorescent perylene bisimide indicators—a platform for broadband pH optodes

Population analysis to increase the robustness of molecular computational identification and its extension into the near-infrared for substantial numbers of small objects

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