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

Li, Yuanyuan; Li, Haowen; Jin, Wenhui; Xu, Xiyan; Liu, Huiying; Yang, Ding; Wang, Gang; Zhang, Tingting; Peng, Qiuchen; He, Juan; Hu, Qingxi; Pan, Li; Li, Kai

doi:10.1016/j.dyepig.2022.110295

Cited by 24 publications

(20 citation statements)

References 26 publications

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“…However, an enhanced ESIPT effect obtained from the Schiff base derivatives critically hinders the reversible process, which also explains why AN‐pht can barely recover to its initial state even under white‐light illumination for a long time (Figures 5F and S22). A similar photoisomerization performance is observed for previously reported Schiff base derivatives [16, 17] …”

Section: Resultssupporting

confidence: 87%

ESIPT‐Inspired Dual‐Mode Photoswitches with Fast Molecular Isomerization in the Solid State

et al. 2023

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Photoswitchable materials have attracted considerable attention in various fields. Developing excellent solid‐state dual‐mode photoswitches is an important but challenging task. Herein, we propose a new strategy to construct an excited‐state intramolecular proton transfer (ESIPT) inspired photoswitch (DiAH‐pht) that possesses aggregation‐induced emission (AIE) features and displays a fast molecular isomerization process characterized by dual‐mode behavior in the solid state. Mechanistic studies indicate that introduction of a bulky group can create a folded molecular conformation that provides adequate volume to facilitate photoisomerization and the enhanced ESIPT effect can boost the isomerization process. The feasibility of our strategy was further demonstrated by the activated photoisomerization performance of the Schiff base derivatives. Furthermore, DiAH‐pht shows good performance in the fields of dual‐mode information encryption and high‐density data storage.

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Section: Resultssupporting

confidence: 87%

ESIPT‐Inspired Dual‐Mode Photoswitches with Fast Molecular Isomerization in the Solid State

et al. 2023

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“…Following bacterial strains S. aureus (MTCC-96), B. subtillis (MTCC-442), and S. typhi (MTCC-98), P. aeruginosa (MTCC-441) were used for the antibacterial activity. Among the tested ligands, L 4 showed excellent activity (MIC, 50 μg/mL) against S. aureus, which is comparable to standard drug Ciprofloxacin. However, compound L 2 and L 4 presented moderate activity against S. typhi (MIC, 62.5 μg/mL) and B. subtillis (MIC, 62.5 μg/ mL), respectively.…”

Section: Antibacterial Activitymentioning

confidence: 83%

Synthesis, Characterization, Antimicrobial and Antimalarial Activities of Azines Based Schiff Bases and their Pd(II) Complexes

Meena

Baroliya

2023

Chemistry & Biodiversity

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Herein, we report synthesis, characterization, antimicrobial and antimalarial activities of azines Schiff base ligands (L 1 À L 4 ) and their palladium (II) complexes (C 1 À C 4 ) of [Pd(L)(OAc) 2 ] type. The azine ligands (L 1 À L 4 ) were prepared by condensation of carbonyl compounds with hydrazine hydrate and their complexes by the reaction of palladium acetate with L 1 À L 4 ligands in 1 : 1 molar ratio. The prepared ligands and their complexes were characterized by spectral characterization using 1 H & 13 C-NMR, FT-IR and mass spectral studies, which revealed that the ligands coordinates via azomethine nitrogen and heteroatom or aryl carbon with palladium. Moreover, Schiff bases and their palladium (II) complexes have been screened for their antibacterial (S. aureus, B. subtillis, and S. typhi, P. aeruginosa), antifungal (C. albicans, A. niger, and A. clavatus) and antimalarial (P. falciparum) activities. The Schiff base L 4 showed good results for antibacterial against S. aureus (MIC, 50 μg/mL) and antimalarial against P. falciparum (IC 50 , 0.83 μg/mL). The complex C 1 showed best antibacterial activity (MIC, 62.5 μg/mL) against S. typhi and the complex C 4 exhibited remarkable antimalarial activity (IC 50 , 0.42 μg/mL) among the tested compounds. Thus, azines based ligands and their Pd complexes can be good antimicrobial and antimalarial agents if explored further.

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“…H 2 L was synthesized according to the literature. , A mixture of nicotinic hydrazide (0.0138 g, 0.1 mmol) and 5-bromosalicylaldehyde (0.0202 g, 0.1 mmol) in methanol (6 mL) was heated at 80 °C, refluxed for 2 h, and then cooled to room temperature. The solution was slowly volatilized after filtration.…”

Section: Methodsmentioning

confidence: 99%

“…To date, typical photochromic materials reported are based on viologen, , azobenzene, , spiropyran, diarylethenes, , and Schiff base. − As a kind of electron-deficient compounds, viologen compounds containing pyridine or bipyridyl salts are easy to undergo electron transfer and produce free radicals when combined with other electron donors under irradiation and thermal excitation. − Salicylaldehyde Schiff base can also exhibit excellent thermochromic and photochromic properties with the advantages of facile synthesis, good reversibility, and fatigue resistance, which is mostly used as molecular switches. The reported mechanism mainly depends on the presence of intramolecular hydrogen bonds to generate reversible tautomerism between enol and keto forms. − Although most of the developed organic materials have certain advantages, there are still problems of poor thermal stability and low oxidation resistance. By designing metal complexes, these problems can be alleviated and the properties of materials can be broadened. , …”

Section: Introductionmentioning

confidence: 99%

“…Zn(II) with a d electron structure has the advantages of low toxicity, low cost, abundant reserves, and spectral inertness. − Zn(II) complexes with various geometric coordination configurations have rich photoluminescence and are excellent candidates for the development of low-cost stimuli-responsive materials. − However, the development of single-component complexes simultaneously featuring multi-stimuli-responsive behaviors in different states is still a challenging task. Schiff base with O,N,O-hydrazone shows luminescence architectures with wide possibilities for coordination sites and symmetries. ,− The push–pull electronic properties of the conjugated ligands can be adjusted through structural modification. It is well known that introducing halogen atoms into structures is a widely used method to achieve heavy atom effect, which is conducive to the generation of delayed fluorescence or phosphorescence. − …”

Section: Introductionmentioning

confidence: 99%

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Conformation- and Coordination Mode-Dependent Stimuli-Responsive Salicylaldehyde Hydrazone Zn(II) Complexes

et al. 2023

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Luminescent Zn(II) complexes that respond to external stimuli are of wide interest due to their potential applications. Schiff base with O,N,O-hydrazone shows excellent luminescence properties with multi-coordination sites for different coordination modes. In this work, three salicylaldehyde hydrazone Zn(II) complexes (1, 2a, 2b) were synthesized and their stimuli-responsive behaviors in different states were explored. Only complex 1 exhibits reversible and self-recoverable photochromic and photoluminescence properties in solution. This may be due to the configuration eversion and the excited-state intramolecular proton transfer (ESIPT) process. In the solid state, 2a has obvious mechanochromic luminescence property, which is caused by the destruction of intermolecular interactions and the transformation from crystalline state to amorphous state. 2a and 2b have delayed fluorescence properties due to effective halogen bond interactions in structures. 2a could undergo crystal-phase transformation into its polymorphous 2b by force/vapor stimulation. Interestingly, 2b shows photochromic property, which can be attributed to the electron transfer and generation of radicals induced by UV irradiation. Due to different conformations and coordination modes, the three Zn(II) complexes show different stimuli-responsive properties. This work presents the multi-stimuli-responsive behaviors of salicylaldehyde hydrazone Zn(II) complexes in different states and discusses the response mechanism in detail, which may provide new insights into the design of multi-stimuli-responsive materials.

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

Cited by 24 publications

References 26 publications

ESIPT‐Inspired Dual‐Mode Photoswitches with Fast Molecular Isomerization in the Solid State

ESIPT‐Inspired Dual‐Mode Photoswitches with Fast Molecular Isomerization in the Solid State

Synthesis, Characterization, Antimicrobial and Antimalarial Activities of Azines Based Schiff Bases and their Pd(II) Complexes

Conformation- and Coordination Mode-Dependent Stimuli-Responsive Salicylaldehyde Hydrazone Zn(II) Complexes

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