Merocyanines with embedded butadiene structure in a cyclohexane scaffold are readily obtained by consecutive three-component alkynylation-addition sequences in moderate to excellent yield. Moreover, employing pyrrolidine as an amine provides a pseudo...
Polarizable continuum methods (PCM) have been widely employed for simulating solvent effects, in spite of the fact that they either ignore specific interactions in solution or only partially reproduce non-specific contributions. Examples of three sol...
This joint experimental-theoretical work focuses on molecular and photophysical properties of the spiropyran-containing amphiphilic molecule in organic and aqueous solutions. Being dissolved in tested organic solvents, the system demonstrates positiv...
The potential of E–Z photoisomerization in molecular organic light-to-thermal conversion and storage in an E–styryl merocyanine system was studied in a polar acidic medium. A photoswitchable styryl merocyanine dye (E)-2-(2-(2-hydroxynapht...
This research focuses on the merocyanine form of a new synthesized spiroindolinonaphthoxazine compound. The merocyanine molecule (abbreviated as MC) has multiple fragments with different degrees of mobility. The conformational changes and the flexibi...
The 5-(4-substituted-arylidene)-1,3-dimethylpyrimidine-2,4,6-triones were tested as visible light sensitizers for phenyltrialkylborate salts applied to initiate polymerization processes. The initiation occurs as a result of photoinduced electron tran...
Low-molecular-weight peptide gelators are a versatile class of compounds able to form gels under a variety of conditions, even via simple ultrasound sonication. In this paper, the ability of Boc-L-Phe-D-Oxd-L-Phe-OBn to gelate three organic solvents...
Mechanically induced spiropyran (SP)–merocyanine (MC) interconversion was examined using the enforced geometry optimization (EGO) method at the B3LYP/6-311G(d,p) level. The calculations followed a complete mechanical cycle for the SP–CH3...
This work demonstrates by means of DFT and ab initio calculations that recognition of alkali cations can be achieved by probing the variations of the second-order nonlinear optical properties along the commutation process in spiropyran/merocyanine sy...
A merocyanine dye as a p-toluenesulfonate salt was synthesized. The structure of the dye was characterized using IR, NMR, HR-MS and single crystal X-ray crystallography. The X-ray crystallographic studies revealed the formation of a stacked aggregate...
Two novel, water-soluble, merocyanine fluorophores were readily prepared by microwave-assisted synthesis. Full optical characterization was performed in a series of protic and aprotic solvents, and the dyes displayed fluorescence in the red region wi...
Spiropyran (SP)–Merocyanine (MC) systems represent versatile molecular switches, with their open–closed equilibrium can be finely tuned by their structural characteristics. In this study, we combined conformational sampling, DFT (Density...
A straightforward approach for the construction of the new class of conjugated pyrans based on enamination of 2-methyl-4-pyrones with DMF-DMA was developed. 2-(2-(Dimethylamino)vinyl)-4-pyrones are highly reactive substrates that undergo 1,6-conjugat...
In this paper, the relaxation isomerization properties of a spiropyran-doped poly(methyl methacrylate) (PMMA) UV light-responsive dynamic material are presented. The polar liquid (acetonitrile) and solid (PMMA matrix) medium may contain two merocyani...
Advances in electronics and medical diagnostics have made organic dyes extremely popular as key functional materials. From a practical viewpoint, it is necessary to assess the spectroscopic and physicochemical properties of newly designed dyes. In th...
Density Functional Theory (DFT) calculations have been performed on the TTC→TTT isomerization reaction of the open forms of the 1',3'-dihydro-8-bromo-6-nitro- 1',3',3'-trimethylspiro[2H-1-benzopyran-2,2'-(2H)indole (8-Br-6-nitro-BIPS) system. The cal...
Stimuli-responsive materials based on renewable biopolymers are highly attractive for developing sustainable chemical sensors. Here, two spiropyran derivatives (SP1 and SP2) were synthesized and covalently grafted onto cellulose, yielding the functio...
A reversible photo-driven sensor for aluminum ions based on photochromicspiropyran was reported with rapid response time. The detection of aluminum wasperformed via the chelation of aluminum ions with the merocyanine form (MC) ofphotochromic spiropyr...
The Suzuki coupling Knoevenagel condensation one-pot synthesis of boronic acids/esters, (hetero)aromatic bromo aldehydes and methylene active compounds is a highly practical consecutive three-component process to provide substance libraries with 60 d...
Micro-capillaries, capable of light-regulated binding and qualitative detection of divalent metal ions in continuous flow, have been realised through functionalisation with spiropyran photochromic brush-type coatings. Upon irradiation with UV light,...
Solvent polarity is important data being used in solvent selections for preliminary engineering design of chemical processes. In this work, a predictive model is proposed for estimating the solvatochromic polarity of electronic transition energy (ET)...
The most important area of modern pharmacology is the targeted delivery of drugs, and one of the most promising classes of chemical compounds for creating drugs of this kind are the photochromic spiropyrans, capable of light-controlled biological act...
Magnesium ions (Mg2+) play an important role in mammalian cell function; however, relatively little is known about the mechanisms of Mg2+ regulation in disease states. An advance in this field would come from the development of selective, reversible...
Due to their ability to reversibly isomerize under the influence of external stimuli, spiropyrans represent the most interesting class of organic photochromic molecules. The photochromic properties of the isomeric forms of spiropyrans differ signific...
In this work, we present a novel spiropyran–containing photochromic pyrrolidinofullerene as a promising agent for the photodynamic therapy of cancer.
New salts of photochromic indoline spiropyrans capable of reversibly responding to UV radiation were synthesized to develop light-controlled materials. Photoinduced reactions of the synthesized compounds were studied using absorption and luminescence...
For the first time a pyrrolidinofullerene salt containing a spiropyran group and an ammonium group, capable of reversibly reacting to UV radiation, has been synthesized. Photoinduced reactions of the synthesized compounds were studied using absorptio...
Petrosamine (1)—a colored pyridoacridine alkaloid from the Belizean sponge, Petrosia sp., that is also a potent inhibitor of acetylcholine esterase (AChE)—was investigated by spectroscopic and computational methods. Analysis of the petros...
A new class of thermochromic polynorbornene with pendent spiropyran moieties has been synthesized. Functionalization of norbornene monomers with spirobenzopyran moieties has been achieved using Steglich esterification. These new monomeric materials w...
Reactions of benzoquinone with amines can potentially lead to the formation of coupled merocyanine or merocyanine/polymethine systems. In this study, several diamino-substituted 1,4-benzoquinones were synthesized. The crystal structures for three der...
Methods for preparation of 5′-substituted spiropyrans, their chemical properties, and the effects of various factors on the relative stabilities of the spiropyrans and their isomeric merocyanine forms are examined, reviewed, and discussed.
Photoswitchable spiropyran has been conjugated to the crowned ring system DO3A, which improves its solubility in dipolar and polar media and stabilizes the merocyanine isomer. Adding the lanthanide ion gadolinium(III) to the macrocyclic ring system l...
A novel technique for the covalent attachment of a light-responsive spiropyran onto polyamide thin film composite nanofiltration (NF) membranes in a one-step reaction using low-energy electron beam technology is described. The effect of illumination...
A new class of 4H-imidazoles was synthesized starting from fused-ring aromatic dinitriles. Strong bathochromic shifts of the longest wavelength absorptions were observed in the corresponding UV/vis spectra due to a conversion of the merocyanine chrom...
Dehydroacetic acid and triacetic acid lactone are known to be versatile substrates for the synthesis of a variety of azaheterocycles. However, their fluorinated analogs were poorly described in the literature. In the present work, we have investigate...
Spiropyrans modified with reactive polyfunctional substituents are of great interest as building blocks for the creation of various smart systems with controllable properties for materials science and biomedicine. In this study, a new highly modified...
This review focuses on block copolymers featuring different photo-responsive building blocks and self-assembly of such materials in different selective solvents. We have subdivided the specific examples we selected: (1) according to the wavelength at...
In this work, high-temperature pyrolysis was used to prepare both the core and shell of lantha-nide-doped UCNPs with lithium yttrium tetrafluoride (LiYF4) to enhance the green luminescence. Merocyanine 540 (MC540)-grafted magnetic nanoparticles were...
A π-conjugated polymer containing spiropyrans (SPs), which could be almost completely converted to protonated merocyanines (MCH+) and back to the SP form by adding an acid and a base, respectively, was developed. The insulation of the π-conjuga...
γ-Glutamyl-cysteinyl-glycine (GSH) plays a critical role in maintaining redox homeostasis in biological systems and a decrease in its cellular levels is associated with diseases. Existing fluorescence-based chemosensors for GSH acts as irreversible r...
donor–acceptorDonor–acceptor–π–acceptor–donor (D1-A1-π-A2/A3-D2)-type small molecules, such TPA-MC-2 and TPA-MC-3, were designed and synthesized starting from donor-substituted alkynes (TPA-MC-1) via [2 + 2] cycloa...
Very recently, we have reported the synthesis and evaluation of biological properties of new merocyanine dyes composed of triphenylamine moiety, π-aromatic spacer, and rhodanine/2-thiohydantoin-based moiety. Interestingly, 2-thiohydantoin has neve...
Photodynamic therapy (PDT) is a method of cancer treatment that leads to the disintegration of cancer cells and has developed significantly in recent years. The clinically used photosensitizers are primarily porphyrin, which absorbs light in the red...
Shape-shifting polymers usually require not only reversible stimuli-responsive ability, but also strong mechanical properties. A novel shape-shifting photochromic hydrogel system was designed and fabricated by embedding hydrophobic spiropyran (SP) in...
Merophosphinine and phosphinine dyes were reported as phosphorus atom equivalents of merocyanine and cyanine dyes in the 1960s. Although these dyes are excellent sensitizers for enhancing photographic performance, their development has been considera...
Programmed death-ligand 1 protein (PD-L1) has been posited to have a major role in suppressing the immune system during pregnancy, tissue allografts, autoimmune disease and other diseases, such as hepatitis. Photodynamic therapy uses light and a phot...
We present the synthesis and solution properties of dual stimuli-responsive poly(N-isopropylacrylamide-co-spiropyran acrylate) (P(NIPAAm-co-SPA)) copolymers of varying composition prepared via nitroxide-mediated copolymerization. The resulting copoly...
The high sensitivity of silicon microcantilever sensors has expanded their use in areas ranging from gas sensing to bio-medical applications. Photochromic molecules also represent promising candidates for a large variety of sensing applications. In t...
Achieving light-induced manipulation of controlled self-assembly in nanosized structures is essential for developing artificially dynamic smart materials. Herein, we demonstrate an approach using a non-photoresponsive hydrogen-bonded (H-bonded) macro...
Molecular structure is traditionally described in terms of chemical composition, atomic connectivity, and three-dimensional geometry. However, many molecules, particularly biomacromolecules, exist not as single structures but as dynamic ensembles of...
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