An NIR emitting styryl dye with large Stokes shift to enable co-staining study on zebrafish neuromast hair cells

McDonald, Lucas; Dahal, Dipendra; Konopka, Michael; Liu, Qin; Pang, Yi

doi:10.1016/j.bioorg.2019.103040

Cited by 15 publications

(19 citation statements)

References 29 publications

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“…As far as we know, even though the TDDFT/B3LYP theoretical level might not become accurately sufficient to surmount the accurate ordering of the closely spaced excited states, previous theoretical works have revealed the reliability as far as the shape of ESIPT potential energy curves is concerned. [ 71–84 ] That is to say, the theoretical constructed potential energy curves could provide reasonable explanations about excited state dynamical processes. Thus, in this work, we adopt this manner to explore the ESIPT reaction and mechanism for Qu3HC system.…”

Section: Resultsmentioning

confidence: 94%

“…Similar with discussing the ESIPT mechanism of Qu3HC itself above, the investigation about potential energy curve should be a good manner to explore protonated and deprotonated reactions in both ground and excited states. [ 71–84 ] In fact, it could be clearly seen that the potential energy curve decreases along with the shortening of H and F atoms until the length of H–F reaches 1.0 Å. That is to say, the fluoride‐triggered deprotonation reaction happens spontaneously forming the Qu3HC‐A structure in the ground state.…”

Section: Resultsmentioning

confidence: 97%

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Fluoride anion sensing mechanism of 2‐(quinolin‐2‐yl)‐3‐hydroxy‐4H‐chromen‐4‐one chemosensor based on inhibition of excited state intramolecular ultrafast proton transfer

Feng

et al. 2020

J of Physical Organic Chem

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The excited state hydrogen bonding interactions and intramolecular proton transfer (ESIPT) process for 2‐(quinolin‐2‐yl)‐3‐hydroxy‐4H‐chromen‐4‐one (Qu3HC) system has been theoretically studied via density functional theory (DFT) and time‐dependent DFT (TDDFT) methods. We confirmed that the reversible tuning of intramolecular hydrogen bonding direction is impossible for Qu3HC system. Then, we have studied the S0‐state and S1‐state hydrogen bonding dynamical behaviors of Qu3HC structure and confirmed that the strengthening of intramolecular hydrogen bond in the S1 state could facilitate ESIPT reaction. Given photo‐induced excitation, we find that the charge redistribution around hydroxyl moiety plays important roles in providing driving force for ESIPT. Our constructed potential energy curves further verify that the ESIPT process of Qu3HC should be ultrafast due to low potential barrier. With the addition of fluoride anions, the exothermal deprotonation process occurs spontaneously along with the intermolecular hydrogen bond O–H···F, which reveals the uniqueness of detecting fluoride anion using Qu3HC molecule. As a whole, the fluoride anion inhibits the initial ESIPT process of Qu3HC, which results in different fluorescence behaviors.

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Section: Resultsmentioning

confidence: 94%

Section: Resultsmentioning

confidence: 97%

Fluoride anion sensing mechanism of 2‐(quinolin‐2‐yl)‐3‐hydroxy‐4H‐chromen‐4‐one chemosensor based on inhibition of excited state intramolecular ultrafast proton transfer

Feng

et al. 2020

J of Physical Organic Chem

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“…24 The most attractive features of the reported ESIPT−cyanine dyes are their potential in molecular imaging, due to their unique photophysical properties (large Stokes shift), excellent biocompatibility, and high cell penetration ability. [8][9][10]22 The fluorescence of 13b (R 2 = −CH 3 ) was sensitive to its environmental pH, with pK a ≈ 6.01. 22 Benefiting from its large fluorescence turn on upon protonation (Ar−O − + H + → ArOH), probe 13b exhibits selectivity toward intracellular lysosomes similar to that of its regioisomer 8.…”

Section: Esipt-based Fluorescent Probes and Their Applicationsmentioning

confidence: 99%

“…Some molecular probes that emit in the near-infrared (NIR) region are ideal to be developed for analytical and biological applications such as in cell imaging. In comparison with commercial dyes that emit in the UV/vis range, NIR dyes have advantages of deep tissue penetration, less tissue damage, and minimal interference caused by tissue absorption and autofluorescence. − …”

Section: Introductionmentioning

confidence: 99%

“…The proton transfer from the phenol to the −CN– group can be viewed simply as an acid–base reaction, as the phenolic proton is known to become more acidic in the excited state (p K a ∼ 5.7) . The acidity of the phenolic proton could be influenced by a suitable electron-withdrawing or electron-donating substituent, which could actively perturb the proton transfer process. − …”

Section: Introductionmentioning

confidence: 99%

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Progress in Tuning Emission of the Excited-State Intramolecular Proton Transfer (ESIPT)-Based Fluorescent Probes

Dahal

Abeywickrama

et al. 2021

ACS Omega

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In this review, we will summarize our recent progress in the design and application of novel organic sensors with emission in the near-infrared region (600–900 nm). By coupling different functional groups with excited-state intramolecular proton transfer (ESIPT) segments, new probes are developed to achieve a large Stokes shift, high sensitivity, and selectivity and to tune the emission toward the near-infrared region. The developed probes exhibit attractive optical properties for bioimaging and environmental science applications. In addition, we further discuss the photophysical properties of ESIPT dyes and how their fluorescence could be affected by structural/environmental factors, which should be considered during the development of robust ESIPT-based fluorescence probes. Their potential applications as imaging reagents are illustrated for intracellular membranes, mitochondria, lysosomes, and some biomolecules.

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Deep Red to NIR Emitting Xanthene Hybrids: Xanthene‐Hemicyanine Hybrids and Xanthene‐Coumarin Hybrids

Khan

Sekar

2023

ChemistrySelect

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Xanthene dyes exhibit remarkable photophysical properties and photostability. Their ability to switch fluorescence on/off depending on the external environment makes them a promising candidate for imaging/sensing/tracking/labeling probes. However, their emission � 600 nm and Stokes shift ∼ 34 nm restrict their use in biological applications. A wellknown approach to shifting the emission of xanthene dyes in the deep red to Near infrared (NIR) is by forming xanthene hybrids. This review gives a comprehensive list of the deep red to NIR xanthene-hemicyanine and xanthene-coumarin hybrids. We have outlined general synthetic strategies and a detailed discussion of substituent effect, π-conjugation, and ring effect on the photophysical properties of these dyes. A section on applications of deep red to NIR xanthene hybrids based on fluorophore-linker strategy and spirocyclization is included. This review highlights the structure-spectroscopic relationships, which will be useful in designing new deep red to NIR xanthene analogs.

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An NIR emitting styryl dye with large Stokes shift to enable co-staining study on zebrafish neuromast hair cells

Cited by 15 publications

References 29 publications

Fluoride anion sensing mechanism of 2‐(quinolin‐2‐yl)‐3‐hydroxy‐4H‐chromen‐4‐one chemosensor based on inhibition of excited state intramolecular ultrafast proton transfer

Fluoride anion sensing mechanism of 2‐(quinolin‐2‐yl)‐3‐hydroxy‐4H‐chromen‐4‐one chemosensor based on inhibition of excited state intramolecular ultrafast proton transfer

Progress in Tuning Emission of the Excited-State Intramolecular Proton Transfer (ESIPT)-Based Fluorescent Probes

Deep Red to NIR Emitting Xanthene Hybrids: Xanthene‐Hemicyanine Hybrids and Xanthene‐Coumarin Hybrids

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