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Mechanofluorochromism based on BOPIM complexes: The effect of substituents and regulation of the direction of the emission color changes
摘要： Novel boron 2-(2′-pyridyl)imidazole (BOPIM) complexes T1, T2 and T3 with different substituents (including bromo, tert-butyl and methoxyl) on the benzene ring of BOPIM dyes have been designed and synthesized, and their optical properties in both solution and the solid state were investigated and compared. The three compounds exhibited typical intramolecular charge transfer (ICT) characteristics. Solvent-dependent UV-vis absorption, fluorescence emission spectra and quantum chemical calculation indicated a molecular push-pull electronic structure. Their ICT degrees increased with the sequence of T1 < T2 < T3. The analysis of the X-ray crystal structure revealed the twisted molecular conformation of BOPIM dyes. Furthermore, they showed remarkable reversible mechanofluorochromic (MFC) features under mechanical force. It was found that the MFC activities could be tuned easily by changing the substituents on the BOPIM dyes. T1 exhibited emission color change from bright green to yellowish green with a spectral red-shift of only 22 nm under mechanical stimuli, whereas T2 and T3 gave the large spectral red-shifts of 36 and 30 nm. Electronic and steric effects of the substitutes were proved playing significant roles in regulating the ICT effect and intermolecular interactions. More importantly, the remarkable effect of substituents on the MFC behaviors of BOPIM dyes will provide an effective way to obtain novel high-contrast MFC dyes.
关键词： Mechanofluorochromism,Substituent effect,Intramolecular charge transfer,Solid-state fluorescence,BOPIM complexes
更新于2025-11-14 15:26:12
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Aggregation-induced emission (AIE)-active highly emissive novel carbazole-based dyes with various solid-state fluorescence and reversible mechanofluorochromism characteristics
摘要： Three new carbazole-based fluorescent molecules 1-3 functionalized with tetraphenylethene have been successfully synthesized, and these compounds have high thermal stability, and they exhibited different fluorescence in solid states with the superior luminescence quantum yields of 99.04% (1), 98.90% (2) and 39.83% (3). Their aggregation-induced behaviors were explored by the study of photoluminescence spectroscopy. The results showed that luminogens 1-3 exhibited remarkable aggregation-induced emission effect. Furthermore, their distinct mechanical stimulus-responsive fluorescence characteristics were also surveyed by solid-state photoluminescence spectroscopy. Interestingly, the various emitting colors of these luminogens could be changed into the same green, and the repeatabilities of their mechanochromic luminescence behaviors were outstanding, and the powder X-ray diffraction results indicated that the reversible conversion from a crystalline to an amorphous state was responsible for the obvious mechanofluorochromism phenomena of compounds 1-3. This work will be valuable for the exploitation of mechanical-force sensors with typical aggregation-induced emission feature.
关键词： Carbazole,Mechanofluorochromism,Tetraphenylethene,Aggregation-induced emission,Different fluorescence,High thermal stability
更新于2025-11-14 15:23:50
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High-contrast mechanofluorochromism and acidochromism of D-π-A type quinoline derivatives
摘要： New D-π-A type quinoline derivatives (CbzVQ and TPAVQ) were synthesized via Knoevenagel condensation reactions. They exhibited reversible high-contrast mechanofluorochromic (MFC) behavior under grinding/fuming treatment. Taking CbzVQ as an example, its fluorescence could be switched from blue to greyish green by grinding the as-synthesized sample into ground powders, and the fluorescence emission was red-shifted from 449 nm (with shoulders at 475 nm and 520 nm) to 578 nm (with shoulders at ca. 450 nm and 500 nm). Such large shift of the maximal emission peak during MFC processes was rare reported. In addition, the casting films of CbzVQ and TPAVQ emitted blue and green light, respectively, which was turned to red rapidly induced by TFA (trifluoroacetic acid) vapor. Moreover, the emission could be recovered stimulated by TEA (triethylamine) vapor, so the quinoline derivatives exhibited reversible fluorescent sensory properties. TPAVQ showed better performance in the detection of TFA vapor than CbzVQ due to the strong electron-donating ability of triphenylamine compared with carbazole. The detection limit and the decay time of TPAVQ towards TFA vapor were 163 ppb and 0.22 s, respectively. Apparently, the D-π-A type quinoline derivatives are candidates as multi-stimuli responsive fluorescent materials.
关键词： carbazole,quinolines,mechanofluorochromism,acidochromism,triphenylamine
更新于2025-09-10 09:29:36
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Alkyl chain-dependent cyano-stilbene derivative's molecular stacking, emission enhancement and fluorescent response to the mechanical force and thermal stimulus
摘要： Two cyano-stilbene derivatives with butyl (C4MPA) and octyl groups (C8MPA) were synthesized to investigate the effects of alkyl chains on molecular stacking, emission enhancement, and mechanofluorochromism. The two compounds displayed weak emissions in monomolecular state and emitted an enhanced fluorescence in crystal state. However, the fluorescence quantum yield of C4MPA (19%) was lower than that of C8MPA (76%). Face-to-face dimer stacking was found only in the C4MPA crystal, in which molecules adopted a nonplanar configuration. The C8MPA crystal presented two kinds of antiparallel 1D arrangement. One involved the antiparallel stacking of nonplanar aromatic moieties. The other consisted of coplanar molecules without π-π stacking, which were responsible for the higher luminescence yield. Moreover, the emission of the C4MPA solid was quenched under mechanical force, whereas the C8MPA solid still emitted a strong fluorescence after grinding. C8MPA lost fluorescence when heated at above 60 °C because of its low melting point, and the supercooling viscous liquid without fluorescence was observed even the sample was cooled to room temperature for 10 h, meaning a very slowly crystallization process. Such non-emissive supercooling viscous liquid might rapidly transform into strongly emissive solid under the mechanical force shearing stimulus. Thus, C8MPA films could be used as sensors for mechanical force and thermal stimuli.
关键词： mechanofluorochromism,emission enhancement,molecular stacking,thermal stimulus,cyano-stilbene derivatives,alkyl chains
更新于2025-09-04 15:30:14