Feeling blue: the luminescence of a triarylboron compound has a high quantum yield (at least 0.64) over a wide temperature range (-50 to +100 °C) and changes from green to blue as the temperature is increased. The luminescence color was determined by the population of the two distinct excited-state conformations-a local excited state (high temperature) and a twisted intramolecular charge-transfer state (low temperature).
The color purple: A siloxy‐functionalized benzamide (see picture) is a highly efficient fluoride ion sensor in water. The sensor, which is activated when the OSi bond is cleaved by fluoride ions, provides two independent modes for signal recognition. In colorimetric mode, the fluoride ion concentration is transformed into a fluorescence signal that can be observed directly with the naked eye.
Nanoparticles of intramolecular proton transfer molecule N,N′-bis(salicylidene)-p-phenylenediamine have been prepared with the reprecipitation method in water. The evolving processes have been monitored by means of UV-vis absorption, fluorescence emission, transient emission spectroscopy, and scanning electron microscopy. The fluorescent intensity is increased beyond 60 times in the nanoparticles compared to that in solution. With the increase of aging time, nanoparticles convert spontaneously from spherical to rodlike and finally to beltlike aggregates. A mechanism for the enhanced emission is proposed on the basis of flattened molecules, and a possible model for change of the nanoparticles' shape is also proposed on the basis of theoretical calculations.
A novel class of 2-(2'-hydroxyphenyl)benzothiazole-based (HBT-based) excited-state intramolecular proton-transfer (ESIPT) compounds, N,N'-di[3-Hydroxy-4-(2'-benzothiazole)phenyl]isophthalic amide (DHIA) and N,N'-di[3-Hydroxy-4-(2'-benzothiazole)phenyl]5-tert-butyl-isophthalic amide (DHBIA) has been feasibly synthesized and the properties of their nanoparticles in THF/H2O mixed solvent were investigated. Both compounds were found to exhibit aggregation-induced emission enhancement (AIEE) due to restricted intramolecular motion and easier intramolecular proton transfer in solid state. On identical experimental conditions, the emission of DHBIA aggregates increased more remarkably than that of DHIA. Different aggregation forms of these two organic compounds, due to the steric hindrance of a single tert-butyl group, could be responsible for the notably different degrees of the fluorescence enhancement. Their aggregation modes were investigated on the basis of time-dependent absorption, scanning electron microscope (SEM) images, and molecular modeling with theoretical calculation. The photophysical dynamics were also depicted based on the extremely fast ESIPT four-level cycle.
Several important photophysical properties of the cyanine dye Cy3 have been determined by laser flash photolysis. The triplet-state absorption and photoisomerization of Cy3 are distinguished by using the heavy-atom effects and oxygen-induced triplet --> triplet energy transfer. Furthermore, the triplet-state extinction coefficient and quantum yield of Cy3 are also measured via triplet-triplet energy-transfer method and comparative actinometry, respectively. It is found that the triplet --> triplet (T1-->Tn) absorptions of trans-Cy3 largely overlap the ground-state absorption of cis-Cy3. Unlike what occurred in Cy5, we have not observed the triplet-state T1-->Tn absorption of cis-Cy3 and the phosphorescence from triplet state of cis-Cy3 following a singlet excitation (S0-S1) of trans-Cy3, indicating the absence of a lowest cis-triplet state as an isomerization intermediate upon excitation in Cy3. The detailed spectra of Cy3 reported in this paper could help us interpret the complicated photophysics of cyanine dyes.
A triple fluorescent compound, N-salicylidene-3-hydroxy-4-(benzo[d]thiazol-2-yl)phenylamine (SalHBP), was dispersed in solid polymers and was developed as a white-light-emitting source in LED by using it as the first simple single compound with different configurations. The CIE coordinates were at (0.29, 0.35), close to those of pure white light. To explore speciation mechanisms in this single compound white light, SalHBP was dissolved in protic, nonpolar, and moderate polar solvent, respectively. Upon excitation, blue, green, and yellowish green emissions were observed from the three solutions at various temperatures. The conformation of SalHBP at room temperature was described by a Car-Parrinello molecular dynamics simulation. With the aid of hybrid density functional theory at the B3LYP/TZVP and PBE0/TZVP levels, three observed emission bands of SalHBP were assigned from the five most probable excited state conformations that were derived from four ground state conformations. The effect of solvent on the emission of SalHBP was summarized as a possibility for forming intermolecular hydrogen bonds between solvent and SalHBP molecules and competition between intra- and intermolecular hydrogen bonds.
Fluorescent temperature sensing has received increasing interest in a wide range of fields, including fluid dynamics, micromechanics, and molecular cell biology. Here, a novel series of triarylboron compounds with significant thermosensitive hue transformation and high fluorescent quantum efficiency in wide temperature range is described. It is then demonstrated that fluorescent core/shell microcapsules based on one of the compounds exhibit outstanding temperature response. The microcapsules, dispersed in different liquid or solid media, can serve as highly robust, reliable, and sensitive fluorescent temperature sensors. The sensors are the first example containing a single organic luminophor with a self‐reference feature that can detect on the micro‐ and macroscale from −30 to 140 °C. This finding may open a new avenue to the development of novel fluorescent temperature sensors.
A series of flexible bis(9-anthryldiamine) ligands (L1-L3) linked with alkyl spacers of different chain length was synthesized and characterized, in order to investigate the coordination behavior of these diamine ligands with metal ions (Zn2+, etc.) based on fluorescence measurements. The results showed that, in the case of anthryldiamine ligands bearing two- or four-carbon links, the zinc ion induced a chelation-enhanced fluorescence (CHEF) effect in aqueous media, while a trace amount of water could selectively quench the blue emission of the Zn(II) complex with a three-carbon-linked ligand (1). Meanwhile, the introduction of more water (concentration >11 %) resulted in the formation of a new green luminescent species; the luminescence intensity was enhanced stepwise to a maximum with addition of approximately 30 % water in THF solution. The peak position (centered at approximately 500 nm) and the lifetime measurement (tau=19.59 ns) indicated that the green luminescence was attributable to a novel edge-to-face dimeric conformation ("T-shaped" conformation) of anthracene, and not to the more common face-to-face dimeric conformation. Accordingly, 1H NMR spectroscopic studies in nonaqueous or aqueous solution confirmed this T-shaped conformation, which is consistent with the results of single-crystal X-ray structure analysis and solid-state photoluminescence studies.
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