Study on photophysical properties of intramolecular charge transfer (ICT) compound: 4-(diphenylamino)biphenyl-4′-boronic acid

Pang, Yue Hong; Shuang, Shao Min; Wong, Man Shing; Li, Zhong Hui; Dong, Chuan

doi:10.1016/j.jphotochem.2004.08.001

Cited by 24 publications

(4 citation statements)

References 23 publications

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“…The estimated dipole moment difference is 12.2 D (debye) (slope 9700 ± 990, R 2 > 0.92), based on the assumption that the Onsager cavity radius a equals 5.35 Å, which is half of the optimized distance between the two farthest atoms of the molecule in the direction of charge separation (10.7 Å) − This estimation from the Lippert−Mataga equation is based on the assumption that the photophysical properties of ellipticine can be described by the theory of general solvent effect; hence, it may not hold if specific solvent effects are involved. Actually, Stokes' shifts observed for solvents with a polarity smaller than 0.03 did not follow the trend (Figure b).…”

Section: Resultsmentioning

confidence: 99%

“…To better understand the factors that affect Stokes' shifts of ellipticine, the data points in Figure b can be roughly divided into two groups corresponding to Δ f values smaller than 0.03 and larger than 0.15. In the more polar region (Δ f > 0.15), a linear trend was found and the corresponding dipole moment difference was estimated to be 12.2 D. Such a large dipole moment difference usually indicates the occurrence of intramolecular charge transfer (ICT) induced by the solvent after excitation. ,− Scheme describes the mechanism by which the ICT occurs. In most cases, solvent polarity is believed to be the effect driving an ICT, but for ellipticine, another important factorhydrogen bondingshould be considered as well.…”

Section: Resultsmentioning

confidence: 99%

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Solvent Effect on the Photophysical Properties of the Anticancer Agent Ellipticine

2006

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This paper investigates how solution conditions, especially solvent polarity and hydrogen bonding, affect the fluorescence of ellipticine, a natural plant alkaloid with anticancer activity. A total of 16 solvents that cover a wide range of polarities were tested. The ultraviolet (UV) absorption and fluorescence emission of ellipticine were found to be solvent dependent. The absorption and emission maximum shifted to higher wavelengths (red shift) with increased solvent polarity. The difference in absorption and emission maximum (Stokes' shift) was large, approximately 10,000-11,000 cm-1, in polar solvents (with orientation polarizability Deltaf>0.2) but unusually small, approximately 8900 cm-1, in nonpolar solvents (hexane and cyclohexane). Large Stokes' shifts were due to an intramolecular charge transfer (ICT), which was enabled by large solvent polarity and hydrogen bonding of ellipticine with the solvents. Two transitions were found in the Lippert-Mataga plot between (1) nonpolar and semipolar solvents and between (2) semipolar and polar solvents. The first transition reflected the formation of hydrogen bonds between ellipticine and the solvents whereas the second transition indicated that ellipticine underwent an ICT. In addition, the larger extinction coefficients and the longer lifetime of ellipticine obtained in protic solvents were attributed to the formation of stronger hydrogen bonds. The photophysical response of ellipticine to changes in solvent polarity and hydrogen bond formation could be used to infer the location of ellipticine in a heterogeneous medium, namely liposomes in aqueous solution. A relatively large red shift of emission in liposomes indicated that ellipticine may be in a more polar environment with respect to the lipid bilayer, possibly close to the hydrophilic interface.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Solvent Effect on the Photophysical Properties of the Anticancer Agent Ellipticine

2006

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“…The dipole moments ( μ e – μ g ) between the ground state and the excited state are estimated by the LM function to be about 36.44, 20.54, 10.57, and 12.89 D. Similarly, evident correlation coefficients for the probes were observed in the MR plot. This major difference in the dipole moment from the ground state to the excited state facilitates charge transfer within the probe molecule. − This confirms that the probe has an ICT mechanism that provides the basis for subsequent viscosity responses. The Δ μ of probes HT-SA and HT-SA-S is larger compared to the other probes, which also corresponds to the high solvochromism ability of these two molecules in the above experiments.…”

Section: Resultsmentioning

confidence: 76%

Design and Screening of Fluorescent Probes Based upon Hemicyanine Dyes for Monitoring Mitochondrial Viscosity in Living Cells

Zhang,

Ma,

Zhang

et al. 2024

J. Phys. Chem. B

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Viscosity, at the subcellular level, plays a crucial role as a physicochemical factor affecting microenvironment homeostasis. Abnormal changes in mitochondrial viscosity often lead to various diseases in the organism. Based on the twisted intramolecular charge transfer mechanism, four hemicyanine dye fluorescent probes (HT-SA, HT-SA-S, HT-Bzh, and HT-NA) were designed and synthesized for viscosity response. The single bond between the nitrogen-containing heterocycle and the carbon−carbon double in the structure of the probe bond served as the viscosity response site. Finally, the probe HT-Bzh was screened as the optimal mitochondrial viscosity probe according to its responsiveness, targeting, and interference resistance. The fluorescence intensity of the probe HT-Bzh increased 22-fold when the viscosity was increased from 13.75 to 811.2 cP. In summary, all four viscosity probes we have developed can be used in different applications depending on the external environment, providing a valuable reference for the design of potential tools to address viscosity monitoring in biological systems.

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“…As TICT usually exhibits a significantly higher excited dipole moment than the above, the above increase of the excited state dipole moment indicates the presence of intramolecular charge transfer (ICT) properties in this molecule. 37,42,43 However, molecules are inherently nonspherical, so the assumption of using molecular radius instead of cavity radius in this paper is only an approximation. Since TCy3 showed a good "turn-on" response to viscosity, our previous speculation that DNA blocks the formation of TICT mechanism of TCy3 is further advanced.…”

Section: Dye To Viscosity Responsementioning

confidence: 99%

Cy3 Cyanine Dye with Strong Fluorescence Enhancement for AGRO100 and Its Derivative

Shi

Zhang

et al. 2023

J. Phys. Chem. B

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Nucleic acids, as important substances for biological inheritance, have attracted extensive attention in the biomedical field. More and more cyanine dyes are emerging as one of the probe tools for nucleic acid detection due to their excellent photophysical properties. Here, we discovered that the insertion of the AGRO100 sequence can specifically disrupt the twisted intramolecular charge transfer (TICT) mechanism of the trimethine cyanine dye (TCy3), resulting in a clear "turn-on" response. Moreover, the fluorescence enhancement of TCy3 combined with the T-rich AGRO100 derivative is more obvious. One explanation for the interaction between dT (deoxythymidine) and positively charged TCy3 may be that its outer layer carries the most negative charge. This study provides a theoretical basis for the use of TCy3 as a DNA probe, which has promising applications in the DNA detection of biological samples. It also provides the basis for the following construction of probes with specific ability for recognition.

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Study on photophysical properties of intramolecular charge transfer (ICT) compound: 4-(diphenylamino)biphenyl-4′-boronic acid

Cited by 24 publications

References 23 publications

Solvent Effect on the Photophysical Properties of the Anticancer Agent Ellipticine

Solvent Effect on the Photophysical Properties of the Anticancer Agent Ellipticine

Design and Screening of Fluorescent Probes Based upon Hemicyanine Dyes for Monitoring Mitochondrial Viscosity in Living Cells

Cy3 Cyanine Dye with Strong Fluorescence Enhancement for AGRO100 and Its Derivative

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