Stimuli‐Responsive Naphthalene Diimide as Invisible Ink: A Rewritable Fluorescent Platform for Anti‐Counterfeiting

Kalita, Anamika; Malik, Akhtar H.; Sarma, Neelotpal Sen

doi:10.1002/asia.201901800

Cited by 21 publications

(10 citation statements)

References 60 publications

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“…The development of stimuli-responsive organic fluorescent materials has received tremendous attention as a result of their fundamental research and promising applications in information storage, 1,2 anti-counterfeiting paper, 3,4 sensors [5][6][7] and bioimaging. [8][9][10] In particular, mechanochromic (MC) materials that use mechanical force as a stimulus have been recognized as ideal candidates for preparing anti-counterfeiting labels and pressure-sensitive devices.…”

Section: Introductionmentioning

confidence: 99%

Design of High-Contrast Mechanochromic Materials Based on Aggregation-Induced Emissive Pyran Derivatives Guided by Polymorph Predictions

Wen

Xiao

et al. 2022

CCS Chem

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High contrast mechanochromic materials are prominent candidates for sensor, security and memory applications; however, the development of materials with a large luminescence change (Δλ em >100 nm) under external stimuli is challenging. Considering that polymorphic molecules usually exhibit reversible mechanochromism, polymorph prediction is adopted for the first time to guide the design of high-contrast mechanochromic materials in this study. We designed and synthesized a series of donor-π-acceptor pyran derivatives bearing different electron donors and acceptors as model systems. The polymorph prediction indicated that 4-dicyanomethylene-2,6-distyryl-4H-pyran and 4H-pyran-4-one derivatives had the potential to crystallize in both monomer and π-dimer aggregates, while barbituric acid-based compound tended to pack tightly in all aggregated states. The experimental results agreed well with the prediction that the derivatives potentially possessing both monomer and π-dimer aggregate structures exhibit excellent mechanochromic behavior, whereas the fluorescence difference for the barbituric acid-based compounds is minimal. Moreover, a compound with an excellent fluorescence difference of three colors during reversible mechanochromism was chosen as the candidate for an optical recording material and security ink. This work proposes an effective

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Section: Introductionmentioning

confidence: 99%

Design of High-Contrast Mechanochromic Materials Based on Aggregation-Induced Emissive Pyran Derivatives Guided by Polymorph Predictions

Wen

Xiao

et al. 2022

CCS Chem

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“…Alternatively, restoration of the pristine luminous intensity of 6a (deprotonated–decrypted state) occurs via deprotonation by aqueous NH 3 (NH 4 OH), which repairs conjugation to the linker. Such unprecedented swapping between emission off and on modes via deprotonated conjugated and protonated nonconjugated domains (Figure b) exemplifies the rarest site-specific luminescence modulation among contemporary material. , …”

Section: Results and Discussionmentioning

confidence: 94%

High-Performance Water Harvester Framework for Triphasic and Synchronous Detection of Assorted Organotoxins with Site-Memory-Reliant Security Encryption via pH-Triggered Fluoroswitching

Goswami

Das

Seal

et al. 2021

ACS Appl. Mater. Interfaces

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Atmospheric water harvesting, triphasic detection of water contaminants, and advanced antiforgery measures are among important global agendas, where metal–organic frameworks (MOFs), as an incipient class of multifaceted materials, can affect substantial development of individual properties at the interface of tailor-made fabrication. The chemically robust and microporous MOF, encompassing contrasting pore functionalization, exhibits an S-shaped water adsorption curve at 300 K with a steep pore-filling step near P/P 0 = 0.5 and shows reversible uptake–release performance. Density functional theory (DFT) studies provide atomistic-level snapshots of sequential insertion of H2O molecules inside the porous channels and also portray H-bonding interactions with polar functional sites in the two-fold interpenetrated structure. The highly emissive attribute with an electron-pull system benefits the fast-responsive framework and highly regenerable detection of four classes of organic pollutants (2,4,6-trinitrophenol (TNP), dichloran, aniline, and nicotine) in water at a record-low sensitivity. In addition to solid-, liquid-, and vapor-phase sensing, host–guest-mediated reversible fluoroswitching is validated through repetitive paper-strip monitoring and image-based detection of food sample contamination. Structure–property synergism in the electron transfer route of sensing is justified from DFT calculations that describe the reshuffling of molecular orbital energy levels in an electron-rich network by each organotoxin, besides evidencing framework–analyte supramolecular interactions. The MOF further delineates the pH-responsive luminescence defect repair via site-specific emission modulation, wherein reversibly alternated “encrypted and decrypted” states are utilized as highly reusable anticounterfeiting labels over multiple platforms and conceptualized as artificial molecular switches. Aiming at self-calibrated, advanced security claims, a NOR-OR coupled logic gate is devised based on commensurate fluorescence-cum-real-time synchronous detection of organic and inorganic (HCl and NH3) pollutants.

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“…This confirms the potential of our strategy to be applied for multistate information storage with high storage capacity. Compared with the previous reports in which the dynamic fluorescence patterns were generally achieved by the synthesis of functional molecules, [ 3,12,14,21,32–37 ] our approach allows the formation of the dynamic patterns with classical fluorophores that are inexpensive and approachable. The resolution of fluorescence patterns was investigated by forming fluorescence lines with different widths.…”

Section: Resultsmentioning

confidence: 99%

Static–Dynamic Fluorescence Patterns Based on Photodynamic Disulfide Reactions for Versatile Information Storage

Niu

Zhang

et al. 2021

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Dynamic fluorescence patterns with variable output in response to external stimulus can make the current information storage technologies more flexible and intelligent. Yet it remains a great challenge to create such dynamic patterns because of the complicated synthesis process, high cost, limited stability, and biocompatibility of the functional fluorophores. Herein, a facile approach is presented for creating dynamic fluorescence patterns using the photodynamic surface chemistry based on disulfide bonds. By this method, high‐resolution (≈20 µm) multicolor dynamic fluorescence patterns that are low‐cost and dynamically rewritable can be easily fabricated using classical fluorophores such as fluorescein, rhodamine, and dansyl acid. Owing to the spatio‐temporal controllability of light, the fluorescence patterns can be partly or entirely erased/rewritten on demand, and complex gray‐level fluorescence images with increased information capacity can be easily generated. The obtained fluorescence patterns exhibit little changes after storing in air and solvent environments for 100 days, demonstrating their high stability. In addition, static patterns can also be created on the same disulfide surface using irreversible disulfide–ene chemistry, to selectively control the dynamicity of the generated fluorescence patterns. The authors show the successful application of this strategy on information protection and transformation.

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Stimuli‐Responsive Naphthalene Diimide as Invisible Ink: A Rewritable Fluorescent Platform for Anti‐Counterfeiting

Cited by 21 publications

References 60 publications

Design of High-Contrast Mechanochromic Materials Based on Aggregation-Induced Emissive Pyran Derivatives Guided by Polymorph Predictions

Design of High-Contrast Mechanochromic Materials Based on Aggregation-Induced Emissive Pyran Derivatives Guided by Polymorph Predictions

High-Performance Water Harvester Framework for Triphasic and Synchronous Detection of Assorted Organotoxins with Site-Memory-Reliant Security Encryption via pH-Triggered Fluoroswitching

Static–Dynamic Fluorescence Patterns Based on Photodynamic Disulfide Reactions for Versatile Information Storage

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