Synthesis, Photophysical Properties, and Application of <i>o</i>- and <i>p</i>-Amino Green Fluorescence Protein Synthetic Chromophores

Chen, Yi Hui; Lo, Wei Cheng; Sung, Kung-Bin

doi:10.1021/jo302050y

Cited by 26 publications

(39 citation statements)

References 35 publications

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“…To get the optimized structures of the S 1 excited states of cis ‐ p ‐DMABDI and cis ‐ o ‐DMABDI at the CAM‐TD‐B3LYP/cc‐pVDZ level, several different starting geometries including their planar molecular structures were used initially for the geometry optimization, but they both ended up with only one optimized twisted structure. This is consistent with the experimental result that single fluorescent emission was found for each of them …”

Section: Resultssupporting

confidence: 74%

“…To explore or tune the photophysical properties of the GFP chromophore, chemists prepared p ‐HBDI and its various analogues. Thus, the cis ‐ o ‐ and cis ‐ p ‐ N , N ‐dimethylamino analogues ( cis ‐ p ‐DMABDI and cis ‐ o ‐DMABDI) of GFP chromophore were prepared for their possible interesting photophysical properties (Scheme ) . One of the interesting properties is, unlike the dual fluorescence of p ‐DMABN, they were reported to have single fluorescence, and their fluorescent emissions shift to higher wavelengths when they stay in a more polar solvent .…”

Section: Introductionmentioning

confidence: 99%

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TICT excited states of o‐ and p‐N,N‐dimethylamino analogues of GFP chromophore

Sung

2017

J of Physical Organic Chem

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Even though all the p‐N,N‐dimethylaminobenzonitrile (p‐DMABN), cis‐o‐DMABDI, and cis‐p‐DMABDI (the N,N‐dimethylamino analogues of green fluorescence protein chromophore) have the same electron‐donating N,N‐dimethylamino group, unlike the dual fluorescence of p‐DMABN, both cis‐o‐DMABDI and cis‐p‐DMABDI display single fluorescence. To figure out the interesting phenomena, the CAM‐TD‐B3LYP method and the cc‐pVDZ basis set were used to explore geometries, molecular orbitals, electronic transition, dipole moment, and potential energy surfaces of the S1 excited states of cis‐o‐DMABDI and cis‐p‐DMABDI. We found that the S1 excited states of cis‐o‐DMABDI and cis‐p‐DMABDI are 1(π, π*) charge transfer excited states with twisted structures, where the N,N‐dimethylaminobenzene moiety functions as an electron donor, the methyleneimidazolone moiety serves as an electron acceptor, and the electron donor is linked with the electron acceptor by the C─C single bond (P‐bond). The fluorescent emissions of cis‐o‐DMABDI and cis‐p‐DMABDI predicted by the CAM‐TD‐B3LYP/cc‐pVDZ level are quite consistent with the experimental results. For the cis‐o‐DMABDI and cis‐p‐DMABDI, the S1 locally excited state is less stable than the S1 twisted intramolecular charge transfer state, and the S1 LE state is not a stationary point (global minimum). That is why both cis‐o‐DMABDI and cis‐p‐DMABDI display single fluorescence.

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Section: Resultssupporting

confidence: 74%

Section: Introductionmentioning

confidence: 99%

TICT excited states of o‐ and p‐N,N‐dimethylamino analogues of GFP chromophore

Sung

2017

J of Physical Organic Chem

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“…C ompounds 4 and 5 a – 5 d were synthesized starting with imidazolinone derivative 1 and 2‐aminobenzaldehyde ( 3 ), which were prepared according to methods described in the literature. Compounds 1 and 3 were subjected to the Knoevenagel condensation reaction, which afforded 4 in a yield of 85 % (Scheme ). By using 4 as the precursor, we then strategically designed and synthesized four amino‐substituted derivatives 5 a – 5 d (Scheme ).…”

Section: Resultsmentioning

confidence: 99%

“…The lack of ESIPT reflects the much weaker NH 2 hydrogen bond. Instead, the emission of 4 shows charge‐transfer character and hence solvatochromism, that is, a spectral redshift as the solvent polarity is increased …”

Section: Resultsmentioning

confidence: 99%

“…Accordingly, the replacement of OH by NRH may provide invaluable information relating to N−H‐type ESIPT for a relatively weak hydrogen‐bonding system. Thus, in this study we modified o ‐HBDI by replacing the OH group by various NR−H groups, thereby forming a new series of seven‐membered‐ring N−H hydrogen‐bonded compounds based on 5‐(2‐aminobenzylidene)‐2,3‐dimethyl‐3,5‐dihydro‐4 H ‐imidazol‐4‐one ( 4 and 5 a – 5 d ). Details of the synthesis, characterization, and distinct substituent‐dependent NR−H ESIPT properties of this new system are elaborated in the following sections.…”

Section: Introductionmentioning

confidence: 99%

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N−H‐Type Excited‐State Proton Transfer in Compounds Possessing a Seven‐Membered‐Ring Intramolecular Hydrogen Bond

Chen

Meng

Hsu

et al. 2016

Chemistry A European J

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A series of compounds containing 5-(2-aminobenzylidene)-2,3-dimethyl-3,5-dihydro-4H-imidazol-4-one (o-ABDI) as the core chromophore with a seven-membered-ring N-H-type intramolecular hydrogen bond have been synthesized and characterized. The acidity of the N-H proton and thus the hydrogen-bond strength can be fine-tuned by replacing one of the amino hydrogen atoms by a substituent R, the acidity increasing with increasing electron-withdrawing strength of R, that is, in the order H

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Synthesis and Fluorescence Mechanism of the Aminoimidazolone Analogues of the Green Fluorescent Protein: Towards Advanced Dyes with Enhanced Stokes Shift, Quantum Yield and Two‐Photon Absorption

et al. 2021

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Novel small‐molecular analogues the green fluorescence protein (GFP) chromophore were synthesised to expand and improve this fluorophore family and to deepen the understanding of their fluorescence mechanism. The introduction of an aminophenyl substituent and the repositioning of the hydroxyl group, to enable strong intramolecular hydrogen bonding, not only enhanced fluorescence emission but also resulted in an increased Stokes shift and a considerable redshift. Experimental and computational results described dual fluorescence involving both excited‐state intramolecular proton transfer and internal charge transfer (ESIPT‐ICT) mechanisms. Screening of the pH and the solvent medium revealed a complicated equilibrium involving hydrogen bonding, protonation and deprotonation that influences the absorption and emission spectra. Further improvement of the photophysical properties via the systematic variation of dialkylamino substituents at a single position of the chromophore led to a two‐orders of magnitude enhancement in the quantum yields. In addition, the novel compounds also have significant two‐photon absorption, which widens the possibilities for applications in the field of bioimaging.

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Synthesis, Photophysical Properties, and Application of o- and p-Amino Green Fluorescence Protein Synthetic Chromophores

Cited by 26 publications

References 35 publications

TICT excited states of o‐ and p‐N,N‐dimethylamino analogues of GFP chromophore

TICT excited states of o‐ and p‐N,N‐dimethylamino analogues of GFP chromophore

N−H‐Type Excited‐State Proton Transfer in Compounds Possessing a Seven‐Membered‐Ring Intramolecular Hydrogen Bond

Synthesis and Fluorescence Mechanism of the Aminoimidazolone Analogues of the Green Fluorescent Protein: Towards Advanced Dyes with Enhanced Stokes Shift, Quantum Yield and Two‐Photon Absorption

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