4.7 Article

New cationic spiropyrans with photoswitchable NIR fluorescence

Related references

Note: Only part of the references are listed.
Review Chemistry, Multidisciplinary

A Modern Look at Spiropyrans: From Single Molecules to Smart Materials

Anastasia S. Kozlenko et al.

Summary: This article provides an overview of the recent advances in the synthesis, properties investigation, and applications of spiropyran derivatives. The focus is on the multi-sensitive spirocyclic compounds and their potential applications in various fields including smart material production, molecular electronics, sensing of environmental and biological molecules, and photopharmacology.

TOPICS IN CURRENT CHEMISTRY (2023)

Review Chemistry, Multidisciplinary

Designs and Applications of Multi-stimuli Responsive FRET Processes in AIEgen-Functionalized and Bi-fluorophoric Supramolecular Materials

Chia-Hua Wu et al.

Summary: This review focuses on several popular strategies in designing FRET-OFF/ON mechanisms of ratiometric fluorescence systems, including aggregation-induced emission, supramolecular assemblies, photochromic molecular switches, and surfactant-induced AIE/FRET mechanisms. The strategies and examples provided in this review offer insights and toolkits for future FRET-based material developments.

TOPICS IN CURRENT CHEMISTRY (2023)

Article Chemistry, Analytical

Near-Infrared-Emitting Meso-Substituted Heptamethine Cyanine Dyes: From the Synthesis and Photophysics to Their Use in Bioimaging

Louise Kommers Reimann et al.

Summary: In this study, heptamethine cyanine dyes were synthesized and their meso-substituted derivatives were prepared. These dyes exhibited UV-Vis absorption and NIR fluorescence emission without aggregation in both ground and excited states. The substitution at the meso position played a crucial role in their photophysics, with the main absorption in the green-orange region. The excited state photophysics showed dependence on the excitation wavelengths, complicating the correlation between spectroscopy and structure. Density Functional Theory and OO-SCS-MP2 calculations revealed the significant impact of conjugation effects on the geometries and electronic configurations of these compounds in both ground and excited states. Finally, the fluorescent properties of the meso-substituted heptamethine cyanine dyes were successfully utilized as stable staining probes in biological media.

CHEMOSENSORS (2023)

Article Nanoscience & Nanotechnology

Dual-Color Photoluminescent Functionalized Nanoparticles for Static-Dynamic Anticounterfeiting and Encryption: First Collaboration of Spiropyran and Coumarin

Amin Abdollahi et al.

Summary: Increasing the security of anticounterfeiting materials has become a major challenge in recent years. This study successfully synthesized multi-functional copolymer nanoparticles with different functional groups using the emulsion polymerization method. These nanoparticles were further modified with photochromic and fluorescent derivatives to develop dual-color photoluminescent polymer nanoparticles for anticounterfeiting inks. The investigation of optical properties showed that the polarity of functional groups affected the particle size and morphology of the nanoparticles. Printing security tags on cellulose paper using the developed dual-color photoluminescent inks demonstrated excellent printability, resolution, brightness, and static-dynamic photoluminescence emission with high intensity. The study of dynamic color change in the fluorescence emission opens up new possibilities for advanced and high-security anticounterfeiting technologies.

ACS APPLIED MATERIALS & INTERFACES (2023)

Article Chemistry, Multidisciplinary

Photochemical OFF/ON Cytotoxicity Switching by Using a Photochromic Surfactant with Visible Light Irradiation

Mai Shinohara et al.

Summary: This study investigated the photochemical switching of cytotoxicity by using spiropyran compounds with pyridinium and alkyl groups. The results showed that the two isomers of SP6 (MC and SP) displayed different cytotoxicity under visible light irradiation at different concentrations, achieving the photochemical switching of cytotoxicity. These findings are important for the development of novel photochemotherapy drugs.

ACS OMEGA (2022)

Article Chemistry, Applied

Novel polychromogenic fluorine-substituted spiropyrans demonstrating either uni- or bidirectional photochromism as multipurpose molecular switches

Artem D. Pugachev et al.

Summary: Novel photochromic spiropyrans with fluorine substituents and cationic fragments or formyl groups were synthesized using a simple one-pot method. The structural- related photochromic transformations of the studied SPPs include positive, negative, and balanced photochromism effects, depending on the substituents at different positions on the molecule.

DYES AND PIGMENTS (2022)

Article Chemistry, Multidisciplinary

DFT modeling of indoline spiropyrans with a cationic substituent in the gas phase

Vitaliy V. Koval et al.

Summary: Isomeric forms of indoline spiropyrans exhibit unique behavior compared to similar compounds. Experimental data and DFT modeling in gas phase were used to investigate the intramolecular factors that determine the occurrence of ring opening reaction based on the specific structure of the compound. The study also explores the charge redistributions, changes in geometry, and chemical bonds in the structures.

MENDELEEV COMMUNICATIONS (2022)

Article Multidisciplinary Sciences

Bioorthogonally activatable cyanine dye with torsion-induced disaggregation for in vivo tumor imaging

Xianghan Zhang et al.

Summary: This article presents a method for expanding the repertoire of responsive dyes in biorthogonal chemistry by developing a near-infrared fluorophore that turns on its fluorescence upon biorthogonal reaction. The study discovers a design mechanism for the construction of bioorthogonally activatable NIR fluorophores and demonstrates their potential in sensitive in vivo imaging of tumors.

NATURE COMMUNICATIONS (2022)

Article Materials Science, Multidisciplinary

Single wavelength colour tuning of spiropyran and dithienylethene based photochromic coatings

Ruben Feringa et al.

Summary: The study demonstrates that immobilizing photochromic molecular switches in a PMMA polymer matrix allows for tuning of color and transparency. By utilizing the primary inner filter effect and the layered construction of the films, only a single excitation wavelength is required for photochemical switching.

MATERIALS ADVANCES (2022)

Article Chemistry, Medicinal

Novel molecular hybrids of indoline spiropyrans and α-lipoic acid as potential photopharmacological agents: Synthesis, structure, photochromic and biological properties

Ilya V. Ozhogin et al.

Summary: Organic photochromic compounds are currently of great interest for use in photopharmacology, targeted drug delivery, and bio-imaging. The synthesis of two novel molecular hybrids of indoline spiropyrans and alpha-lipoic acid via an esterification reaction was reported in this study. Photochemical studies revealed the photochromic activity of the spirocompounds, while cytotoxicity tests on HeLa cell cultures showed unpredictable biocompatibility of the hybrids compared to their parent substances. Flow cytometry results demonstrated that the hybrids induced an antioxidant response in model cells, indicating emergent biochemical and signaling antioxidant properties.

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS (2021)

Article Chemistry, Organic

Spiropyrans: molecules in motion

Anastasia S. Kozlenko et al.

Summary: This review focuses on the isomerization reactions of indoline spiropyrans, their potential applications as building blocks in molecular machines and self-organizing ensembles, and the factors affecting system morphology, such as electromagnetic radiation or medium acidity.

CHEMISTRY OF HETEROCYCLIC COMPOUNDS (2021)

Article Chemistry, Organic

Synthesis, optical properties and in vitro cell viability of novel spiropyrans and their photostationary states

Shiva K. Rastogi et al.

Summary: A novel class of spiropyran (SP) compounds were synthesized and shown to isomerize upon UV irradiation to reach a photostationary state (PSS). These compounds exhibited growth inhibition of HeLa cervical cancer cells, with PSS showing around a 14-fold lower IC50 compared to SP.

TETRAHEDRON (2021)

Article Chemistry, Organic

Isomerization and changes of the properties of spiropyrans by mechanical stress: advances and outlook

Artem D. Pugachev et al.

Summary: The review focuses on mechanically sensitive indoline spiropyrans and their structural features, exploring recent advances in their isomerization processes. Special attention is given to the effect of pressure on spiropyrans in photochromic materials and the formation of J-aggregates in Langmuir-Blodgett films.

CHEMISTRY OF HETEROCYCLIC COMPOUNDS (2021)

Article Chemistry, Applied

Semipermanent merocyanines of spirocyclic compounds: Photochromic balance

Anatoly Metelitsa et al.

Summary: New spiropyrans of the benzophenazine series have been obtained through synthesis methods, showing semipermanent merocyanine properties in solution. The spirobenzopyrans of the benzophenazine series exhibit both positive and negative photochromic properties, leading to the realization of a photochromic balance approach.

DYES AND PIGMENTS (2021)

Article Chemistry, Physical

Synthesis, structure and photochromic properties of indoline spiropyrans with electron-withdrawing substituents

Artem D. Pugachev et al.

Summary: Indoline spiropyrans with conjugated cationic vinyl-3H-indolium fragment and their analogues with formyl substituent in the 2H-chromene moiety were synthesized using a simple one-pot method. The structures of the compounds were confirmed using various analytical techniques, including single crystal X-ray. Photochromic properties were studied, showing that electron-withdrawing substituents stabilize merocyanine isomer effectively, while certain substituents can suppress photochromic behavior.

JOURNAL OF MOLECULAR STRUCTURE (2021)

Article Nanoscience & Nanotechnology

Photoluminescent Nanoinks with Multilevel Security for Quick Authentication of Encoded Optical Tags by Sunlight: Effective Physicochemical Parameters on Responsivity, Printability, and Brightness

Amin Abdollahi et al.

Summary: The study focuses on the development of amine-functionalized latex nanoparticles and their surface modification with spiropyran photoswitches to create anticounterfeiting nanoinks with multilevel security and photochromic/fluorescence properties. These nanoinks are used for printing encoded optical security tags on cellulosic papers and banknotes, allowing for easy and fast authentication through sunlight irradiation.

ACS APPLIED MATERIALS & INTERFACES (2021)

Article Chemistry, Physical

Efficient evaluation of electrostatic potential with computerized optimized code

Jun Zhang et al.

Summary: An efficient algorithm for evaluating ESP was proposed, which showed comparable or better performance than some state-of-the-art codes for systems like dopamine and remdesivir. The algorithm exhibited good parallelization scaling and was able to evaluate ESP for a system with 4840 GTOs and 259,262 ESP points in 1874 seconds on ordinary hardware.

PHYSICAL CHEMISTRY CHEMICAL PHYSICS (2021)

Article Chemistry, Multidisciplinary

Photo-controlled bipolar absorption switches based on 5-dimethylamino substituted indoline spiropyrans with semipermanent merocyanines

Anatoly Metelitsa et al.

Summary: New spiropyrans of the indoline series with semipermanent merocyanines have been synthesized, showing both positive and negative photochromism in solution. Photo-controlled bipolar absorption switches based on dimethylamino-substituted spiropyrans have been proposed, with characteristics tunable through structural design and medium parameters.

NEW JOURNAL OF CHEMISTRY (2021)

Article Multidisciplinary Sciences

Near-Infrared Fluorescent pH Responsive Probe for Targeted Photodynamic Cancer Therapy

Siriwalee Siriwibool et al.

SCIENTIFIC REPORTS (2020)

Article Spectroscopy

Visible to near-IR molecular switches based on photochromic indoline spiropyrans with a conjugated cationic fragment

Artem D. Pugachev et al.

SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY (2020)

Article Chemistry, Applied

Benzothiazolyl substituted spiropyrans with ion-driven photochromic transformation

Anatoly Chernyshev et al.

DYES AND PIGMENTS (2020)

Article Chemistry, Physical

The ORCA quantum chemistry program package

Frank Neese et al.

JOURNAL OF CHEMICAL PHYSICS (2020)

Article Chemistry, Multidisciplinary

All-electron scalar relativistic basis sets for the elements Rb-Xe

Julian D. Rolfes et al.

JOURNAL OF COMPUTATIONAL CHEMISTRY (2020)

Article Chemistry, Physical

Noncommutative Switching of Double Spiropyrans

Luuk Kortekaas et al.

JOURNAL OF PHYSICAL CHEMISTRY A (2020)

Article Chemistry, Multidisciplinary

One-Pot Synthesis and Structure Study of a New Indoline Spiropyran with Cationic Substituent

A. D. Pugachev et al.

DOKLADY CHEMISTRY (2019)

Review Polymer Science

Stimuli-chromism of photoswitches in smart polymers: Recent advances and applications as chemosensors

Amin Abdollahi et al.

PROGRESS IN POLYMER SCIENCE (2019)

Review Polymer Science

The light-controlling of temperature-responsivity in stimuli-responsive polymers

Amin Abdollahi et al.

POLYMER CHEMISTRY (2019)

Review Chemistry, Multidisciplinary

The evolution of spiropyran: fundamentals and progress of an extraordinarily versatile photochrome

Luuk Kortekaas et al.

CHEMICAL SOCIETY REVIEWS (2019)

Article Chemistry, Multidisciplinary

Specific detection of hypochlorite: a cyanine based turn-on fluorescent sensor

Soham Samanta et al.

JOURNAL OF CHEMICAL SCIENCES (2019)

Article Chemistry, Inorganic & Nuclear

Spiropyrans for light-controlled drug delivery

Francesca Cardano et al.

DALTON TRANSACTIONS (2019)

Article Chemistry, Multidisciplinary

Repurposing Cyanine NIR-I Dyes Accelerates Clinical Translation of Near-Infrared-II (NIR-II) Bioimaging

Shoujun Zhu et al.

ADVANCED MATERIALS (2018)

Article Chemistry, Organic

AN INDOCYANINE-BASED TURN-ON FLUORESCENT PROBE FOR SPECIFIC DETECTION OF BIOTHIOLS

Xiaojing Wang et al.

HETEROCYCLES (2018)

Article Chemistry, Inorganic & Nuclear

Structure Investigation of New Condensation Products of 1,2,3,3-Tetramethylindolenium with Metoxysubstituted Diformylphenols

M. B. Lukyanova et al.

JOURNAL OF STRUCTURAL CHEMISTRY (2018)

Article Chemistry, Multidisciplinary

A near-infrared fluorescent probe for rapid and selective detection of hydrosulfide and imaging in live cells

Yichen Jiang et al.

RESEARCH ON CHEMICAL INTERMEDIATES (2017)

Article Biochemistry & Molecular Biology

Systematic variation of thiophene substituents in photochromic spiropyrans

Dushanthi S. Dissanayake et al.

PHOTOCHEMICAL & PHOTOBIOLOGICAL SCIENCES (2017)

Article Materials Science, Biomaterials

A spiropyran-coumarin platform: an environment sensitive photoresponsive drug delivery system for efficient cancer therapy

Shrabani Barman et al.

JOURNAL OF MATERIALS CHEMISTRY B (2017)

Article Chemistry, Organic

Comparative Evaluation of Substituent Effect on the Photochromic Properties of Spiropyrans and Spirooxazines

Edward I. Balmond et al.

JOURNAL OF ORGANIC CHEMISTRY (2016)

Review Chemistry, Multidisciplinary

Photochromic magnetic materials based on transition metal oxalate complexes

Sergey M. Aldoshin et al.

RUSSIAN CHEMICAL REVIEWS (2016)

Article Chemistry, Multidisciplinary

A spiropyran-based X-ray sensitive fiber

Kenji Kinashi et al.

CHEMICAL COMMUNICATIONS (2015)

Article Chemistry, Multidisciplinary

SHELXT - Integrated space-group and crystal-structure determination

George M. Sheldrick

ACTA CRYSTALLOGRAPHICA A-FOUNDATION AND ADVANCES (2015)

Article Chemistry, Multidisciplinary

Crystal structure refinement with SHELXL

George M. Sheldrick

ACTA CRYSTALLOGRAPHICA SECTION C-STRUCTURAL CHEMISTRY (2015)

Article Chemistry, Multidisciplinary

Cyanine-Based Fluorescent Probe for Highly Selective Detection of Glutathione in Cell Cultures and Live Mouse Tissues

Jun Yin et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2014)

Article Chemistry, Organic

Photo- and thermochromic spirans. 38. New (1-alkyl-4,5-diphenyl)imidazolyl-substituted spirobenzopyrans

E. V. Solov'eva et al.

CHEMISTRY OF HETEROCYCLIC COMPOUNDS (2013)

Review Chemistry, Multidisciplinary

Light-controlled molecular switches based on bistable spirocyclic organic and coordination compounds

V. I. Minkin

RUSSIAN CHEMICAL REVIEWS (2013)

Article Biochemistry & Molecular Biology

Antiplasmodial activity of novel keto-enamine chalcone-chloroquine based hybrid pharmacophores

Koneni V. Sashidhara et al.

BIOORGANIC & MEDICINAL CHEMISTRY (2012)

Article Chemistry, Multidisciplinary

Multiwfn: A multifunctional wavefunction analyzer

Tian Lu et al.

JOURNAL OF COMPUTATIONAL CHEMISTRY (2012)

Article Chemistry, Physical

The investigation of the intermediates of spiropyran retinal analogs by laser flash photolysis techniques with different excitation wavelengths

Peter P. Levin et al.

JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY A-CHEMISTRY (2012)

Article Chemistry, Multidisciplinary

Effect of the Damping Function in Dispersion Corrected Density Functional Theory

Stefan Grimme et al.

JOURNAL OF COMPUTATIONAL CHEMISTRY (2011)

Article Chemistry, Multidisciplinary

Ultrafast Bidirectional Photoswitching of a Spiropyran

Johannes Buback et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2010)

Software Review Chemistry, Multidisciplinary

OLEX2: a complete structure solution, refinement and analysis program

Oleg V. Dolomanov et al.

JOURNAL OF APPLIED CRYSTALLOGRAPHY (2009)

Review Chemistry, Physical

Double-hybrid density functional theory for excited electronic states of molecules

Stefan Grimme et al.

JOURNAL OF CHEMICAL PHYSICS (2007)

Article Chemistry, Organic

Synthesis and properties of benzophenone-spiropyran and naphthalene-spiropyran conjugates

Massimiliano Tomasulo et al.

JOURNAL OF ORGANIC CHEMISTRY (2007)

Article Chemistry, Physical

Semiempirical hybrid density functional with perturbative second-order correlation

S Grimme

JOURNAL OF CHEMICAL PHYSICS (2006)

Article Chemistry, Physical

Comprehensive theoretical study of the conversion reactions of spiropyrans: Substituent and solvent effects

YH Sheng et al.

JOURNAL OF PHYSICAL CHEMISTRY B (2004)

Article Chemistry, Multidisciplinary

Energies, structures, and electronic properties of molecules in solution with the C-PCM solvation model

M Cossi et al.

JOURNAL OF COMPUTATIONAL CHEMISTRY (2003)

Article Chemistry, Physical

A photochromic molecule-based magnet

S Benard et al.

CHEMISTRY OF MATERIALS (2001)

Article Chemistry, Physical

Energy barrier to TTC-TTT isomerisation for the merocyanine of a photochromic spiropyran

J Hobley et al.

PHYSICAL CHEMISTRY CHEMICAL PHYSICS (2000)