Role of Nonfluorescent Twisted Intramolecular Charge Transfer State on the Photophysical Behavior of Aminophthalimide Dyes

Soujanya, T.; Fessenden, Richard W.; Samanta, Anunay

doi:10.1021/jp9526509

Cited by 161 publications

(189 citation statements)

References 32 publications

Supporting

Mentioning

171

Contrasting

Unclassified

Order By: Relevance

“…[52,[63][64][65] Clearly, this is a possibility here as indicated by behavior in NMR spectroscopic experiments at various temperatures. To investigate the large Stokes shifts observed for 12 and 13, the change to the conformation of 13 in its first singlet excited state relative to the ground-state structure was calculated.…”

mentioning

confidence: 87%

Naphthyridyl‐Substituted 4,4‐Difluoro‐4‐bora‐3a,4a‐diaza‐s‐indacene (BODIPY) Luminophores: Photophysics and Application as Molecular Imaging Probes in Live Cells

et al. 2013

View full text Add to dashboard Cite

The synthesis, optical properties, and cellular uptake of a family of 4,4‐difluoro‐4‐bora‐3a,4a‐diaza‐s‐indacene (BODIPY) derivatives that incorporate a naphthyridine substituent at the 8‐position of the BODIPY core and either alkyl, bromo, or dimethylamino aryl groups at the 2‐ and 6‐positions are described. The family of compounds is classified, based on their optical properties, into two types; Class I, compounds with alkyl substituents at the 2‐ and 6‐positions show intense solvent‐independent emission, which arises from the BODIPY core with no involvement of the naphthyridine. Class II, the dimethylaminoaryl‐containing compounds exhibit charge transfer transitions that lead to NIR fluorescence and remarkably large Stokes shifts, which make them potentially attractive in bioimaging. Class II compounds exhibit complex solvent dependence. There is evidence for dual fluorescence from multiple rotamers; this is rationalized with the aid of time‐dependant density functional theory (TDDFT) calculations. A representative compound from each class was PEGylated, which rendered them water soluble, but their photophysical properties were maintained in aqueous buffered media. The uptake of the PEGylated BODIPY compounds and the nonPEGylated parent compounds by live mammalian cells was compared by using confocal fluorescence microscopy and resazurin blue cytotoxicity assays were performed. All compounds tested exhibited good cell uptake, were largely nuclear excluding, and had low toxicity at 10 μM. This is to our knowledge the first demonstration of such a mega‐Stokes‐shifted BODIPY probe in cell imaging.

show abstract

mentioning

confidence: 87%

Naphthyridyl‐Substituted 4,4‐Difluoro‐4‐bora‐3a,4a‐diaza‐s‐indacene (BODIPY) Luminophores: Photophysics and Application as Molecular Imaging Probes in Live Cells

et al. 2013

View full text Add to dashboard Cite

show abstract

“…The linear relationship suggests the presence of just one excited state. These results indicated that the  e (dipole moment of 6 in the excited state) should be a little larger than the  g (the dipole moment of 6 in the ground state) because a positive solvatochromic effect was observed in the absorption spectra and emission spectra [51,52].…”

Section: Photophysical Propertiesmentioning

confidence: 91%

Synthesis and fluorescence emission properties of 1,3,6,8-tetraarylpyrenes

Feng

Tomiyasu

et al. 2013

Journal of Molecular Structure

View full text Add to dashboard Cite

show abstract

“…15 Thus, TMST was thought to be an appropriate compound to study the real viscosity of ionic liquid and the polarity of ionic liquid from the point of view of microviscosity and bulk viscosity. The measured viscosity of ionic liquid [bmim][PF 6 ] (260 cP) 16 used in these experiments as a solvent is much higher than that of acetonitrile (0.34 cP), 16 18 but is almost equivalent with the value of methanol (55.0). 18 In other words the viscosity of this ionic liquid is much higher than that of acetonitrile, but the polarity in E T (30) value is almost the same with that of alcohol and acetonitrile.…”

mentioning

confidence: 99%

“…The measured viscosity of ionic liquid [bmim][PF 6 ] (260 cP) 16 used in these experiments as a solvent is much higher than that of acetonitrile (0.34 cP), 16 18 but is almost equivalent with the value of methanol (55.0). 18 In other words the viscosity of this ionic liquid is much higher than that of acetonitrile, but the polarity in E T (30) value is almost the same with that of alcohol and acetonitrile. Figure 4 shows absorption, fluorescence, and fluorescence excitation spectra of trans-TMST in ionic liquid, [bmim] [PF 6 ].…”

mentioning

confidence: 99%

Photoisomerization and Fluorescence Characteristics of Tetramethoxystilbene in Ionic Liquid

Tamura¹,

Arai²

2011

Chemistry Letters

View full text Add to dashboard Cite

Photochemical behavior of 3,3¤,5,5¤-tetramethoxystilbene (TMST) has been explored in ionic liquid. Two fluorescence components with the lifetime of 4.3 and 23.0 ns were observed for trans-TMST in ionic liquid solution. From this experimental evidence one could propose that ionic liquid may provide two different environments with highly different polarity, nonpolar and highly polar environments.We have been studying photoresponsive materials having C=C double bonds as a basic chromophore of photochemical reactions. 1 As to the usual aromatic compounds we have revealed that the photoisomerization properties such as quantum yield of isomerization and isomerization selectivity are controlled by the excited state energy of the substituent of the aromatic groups substituted at the C=C double bond. In order to develop different photoresponsive compounds we are interested in exploring more complex molecules such as high-molecularweight compounds as well as functionalized molecules by intermolecular 2 or intramolecular 3 5 hydrogen bonding. In the study of high-molecular-weight dendritic compounds, we have prepared water-soluble compounds related to unimolecular micelles as well as compounds soluble in organic solvent. Particularly, for water-soluble stilbene dendrimers we could afford nanoscale unimolecular compounds which have hydrophobic interior and hydrophilic exterior and found several unprecedented photochemical reactions such as highly selective almost one-way trans-to-cis photoisomerization in water. 6 Aromatic C=C compound with hydrogen bonding also exerted interesting photochemical properties showing one-way trans-to-cis isomerization induced by ultrafast intramolecular hydrogen atom transfer in the excited state. 7 As another approach to functionalizing molecules with C=C double bonds we are interested in introducing potentially ionic salts in photoresponsive compounds such as stilbene. Some of the work concerning photoresponsive ionic liquid has been published by us 8,9 for stilbene and by Kawai et al. 10,11 for azobenzene as chromophore. We should briefly mention that ionic liquid is fluid despite being composed of anions and cations and is very much different from inorganic salts which have considerably high melting point.In a previous paper, stilbene ionic liquids with imidazolium cation directly or indirectly attached to the benzene ring at the C=C double bond (Figure 1) have been prepared and it has been found that most of these ionic compounds are ionic liquids either at room temperature or below 100°C. 8,9 Furthermore, cis ionic liquids are all nonfluorescent and trans ionic liquids are all fluorescent and therefore, one can photochemically switch the fluorescence properties as well as morphology of either liquid or solid. Moreover, the stilbene-like compounds are easily isolated as pure cis-and trans-isomers and are stable at room temperature, and therefore we have proposed that the previously reported studies may help to understand the basic properties of stilbene ionic liquids and give some directi...

show abstract

Role of Nonfluorescent Twisted Intramolecular Charge Transfer State on the Photophysical Behavior of Aminophthalimide Dyes

Cited by 161 publications

References 32 publications

Naphthyridyl‐Substituted 4,4‐Difluoro‐4‐bora‐3a,4a‐diaza‐s‐indacene (BODIPY) Luminophores: Photophysics and Application as Molecular Imaging Probes in Live Cells

Naphthyridyl‐Substituted 4,4‐Difluoro‐4‐bora‐3a,4a‐diaza‐s‐indacene (BODIPY) Luminophores: Photophysics and Application as Molecular Imaging Probes in Live Cells

Synthesis and fluorescence emission properties of 1,3,6,8-tetraarylpyrenes

Photoisomerization and Fluorescence Characteristics of Tetramethoxystilbene in Ionic Liquid

Contact Info

Product

Resources

About