Tuning of reversible thermochromic properties of salicylaldehyde Schiff bases through the substitution of methoxy and nitro groups

Shi, Mengyu; Xu, Chunjian; Yang, Zhihong; Wang, Lei; Tan, Shujuan; Xu, Guoyue

doi:10.1016/j.molstruc.2019.01.012

Cited by 7 publications

(7 citation statements)

References 33 publications

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“…Shi et al . reported another series of four salicylaldehyde Schiff bases (Figure , structure 24 ) that show a change in color with temperature . Molecule 24 becomes more red in color increasing the temperature from 25 °C to ca.…”

Section: Emission Band Shiftmentioning

confidence: 99%

“…Another common method for avoiding the concentration dependence of intensity‐based temperature probes is to track changes in the emission wavelength maximum. A molecule's emission wavelength can be impacted by temperature due to conformational changes in the molecule, aggregation, or activation of alternative vibrational bands or spin states . One molecule that exhibits conformational changes upon heating is dipyren‐1‐yl(2,4,6‐triisopropylphenyl)‐borane (Figure , structure 22 ) …”

Section: Emission Band Shiftmentioning

confidence: 99%

“…Schiff bases are also utilized as color changing thermo‐probes based on conformational changes . Ibarra‐Rodríguez et al .…”

Section: Emission Band Shiftmentioning

confidence: 99%

“…After submitting the compounds to 50 heating‐cooling cycles, absorption measurements demonstrated that only one had experienced decomposition. The change in color stems from a change in the functional group from an enol‐imine to a ketone‐amine with increasing temperature . In both of these cases, though temperature changes do elicit a color change, utilizing the compound as a thermometer for determining a specific temperature was not explored.…”

Section: Emission Band Shiftmentioning

confidence: 99%

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Latest Trends in Temperature Sensing by Molecular Probes

et al. 2020

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In this Review, we summarize the work in the last ten years on the development of fluorescent molecular probes with possible applications in microscopic thermometry. We discuss four principal types of temperature‐dependent photoluminescence features: 1) Emission intensity; 2) Ratio of emission intensities; 3) Emission peak shift; and 4) Emission lifetime. We compare the advantages, limitations, and challenges of the different probes using these types of sensing mechanisms. By focusing on molecular probes, rather than nanoparticles or polymers, the mechanisms of temperature dependence are discussed thoroughly, with the most common including twisted intramolecular charge transfer (TICT), aggregation‐induced emission (AIE), and mechanically induced change in emission (MICE). With many different confounding variables associated with each experimental method and mechanism of temperature‐dependent photoluminescence, lanthanide and transition metal complexes seem to be promising candidates for future microscopic thermometry applications.

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Section: Emission Band Shiftmentioning

confidence: 99%

Section: Emission Band Shiftmentioning

confidence: 99%

“…Schiff bases are also utilized as color changing thermo‐probes based on conformational changes . Ibarra‐Rodríguez et al .…”

Section: Emission Band Shiftmentioning

confidence: 99%

Section: Emission Band Shiftmentioning

confidence: 99%

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Latest Trends in Temperature Sensing by Molecular Probes

et al. 2020

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“…A Schiff base (SA) and its derivatives are a representative heat-induced structural isomerization compound, and the thermodynamic stable state of which are of the keto type . Distinctively, the thermochromism of o -hydroxy salicylic aldehyde ( o -HSA) is based on the excited-state intramolecular proton transfer (ESIPT) mechanism of planar molecules (Figure S2); through the pre-existing intramolecular hydrogen-bond configuration, the proton would transfer from the hydroxyl group (amino group) to the imine nitrogen (carbonyl oxygen) under thermal stimulation, which causes a reversible isomerization reaction between the keto type and enol type in the intramolecular structure. , The ESIPT mechanism-based H-bond interaction is often considered for stimulus-responsive materials; for example, Su et al prepared an amphipathic microporous Zn(hpi 2 cf)(DMF)(H 2 O) (hpi 2 cf = 5-(2-(5-fluoro-2-hydroxyphenyl)-4,5-bis(4-fluorophenyl)-1 H -imidazol-1-yl)isophthalic acid), which undergoes single-crystal-to-single-crystal transformation driven by a reversible removal/uptake of coordinating water molecules and then can turn the ligand ESIPT process on or off, resulting in sensitive two-color photoluminescence switching over cycles .…”

Section: Introductionmentioning

confidence: 99%

Thermal-Response Proton Conduction in Schiff Base-Incorporated Metal–Organic Framework Hybrid Membranes under Low Humidity Based on the Excited-State Intramolecular Proton Transfer Mechanism

Zhang

Lin

et al. 2023

ACS Appl. Mater. Interfaces

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Stimulus-responsive proton conduction materials have attracted enormous interest as a new kind of “smart material”. It is desirable to develop the appropriate stimulus signal and high proton-conducting materials with an excellent proton-conducting switch ratio (γ), but it remains a great challenge. Here, it can be found for the first time that 4-((2-hydroxybenzylidene)amino)benzenesulfonic acid (HBABSA) has obvious thermal isomerization when porous solids act as matrixes at the ambient temperatures, which is different from that in the crystalline state at 77 K. Therefore, we proposed a host–guest metal–organic framework (MOF) composite, namely, MOF-808 incorporated with HBABSA (HBABSA@MOF-808), which has a proton-conducting switch ratio (γ) of 16 between 338 and 343 K due to the thermally induced isomerization of HBABSA molecules in the MOF pores. The strong binding between the keto-type HBABSA and MOF at the relatively low temperatures can efficiently suppress the proton conduction, while the enol-type one provides more mobile protons for conduction at the high temperatures due to the excited-state intramolecular proton transfer mechanism. Further, the HBABSA@MOF-808 as a filler is blended into polyvinyl alcohol and poly(2-acrylamide-2-methyl-1-propane sulfonic acid) to form hybrid membranes. The hybrid membrane with the highest content of the MOF composite displays a high proton conductivity of 5.57 × 10–3 S·cm–1 under 353 K and 57% RH along with a good switch ratio of 5.4. The development of thermal-response proton-conducting MOF materials is opening up a unique pathway for remote control, thermal sensing, intelligent batteries, and other fields.

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π-π stacking controlled photochromic/thermochromic properties of salicylaldehyde Schiff base in solid state

Jin

et al. 2022

Dyes and Pigments

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Tuning of reversible thermochromic properties of salicylaldehyde Schiff bases through the substitution of methoxy and nitro groups

Cited by 7 publications

References 33 publications

Latest Trends in Temperature Sensing by Molecular Probes

Latest Trends in Temperature Sensing by Molecular Probes

Thermal-Response Proton Conduction in Schiff Base-Incorporated Metal–Organic Framework Hybrid Membranes under Low Humidity Based on the Excited-State Intramolecular Proton Transfer Mechanism

π-π stacking controlled photochromic/thermochromic properties of salicylaldehyde Schiff base in solid state

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