Solvatochromism and solvent polarity scales

Buncel, Erwin; Rajagopal, Srinivasan

doi:10.1021/ar00175a004

Cited by 281 publications

(142 citation statements)

References 51 publications

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“…28,29 Recently, a variety of solvatochromic molecules with D-A structures including symmetrical or asymmetrical benzothiadiazide based cyanosubstituted diphenylethene derivatives 26,30,31 have been synthesized and studied due to their applicability as probes for the determination of volatile solvent vapor as well as their potential application in optical recording and security papers. These compounds exhibit remarkable solvatochromic and vapochromic characteristics by conjugation effects, molecular packing and conversion of crystalline to amorphous states.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, characterization, aggregation-induced emission, solvatochromism and mechanochromism of fluorinated benzothiadiazole bonded to tetraphenylethenes

Hsu

Weng

2018

RSC Adv.

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Compounds consisting of unsubstituted, monofluoro and difluoro substituted benzothiadiazole bonded to two tetraphenylethenes were successfully prepared by palladium catalyzed Suzuki-Miyaura cross-coupling reaction of their corresponding co-monomers. All compounds exhibited aggregation-induced emission characteristics when the water fraction was higher than 60% in the THF/water mixtures. The emission maximum for the three compounds was blue-shifted when the water content reached 90% compared to that in THF solution. The intensity of emission maximum of difluorinated benzothiadiazole linked with two tetraphenylethenes was 2.5 times higher in 90% water compared to those in THF solution.Surprisingly, two liquid crystal phases with two distinct emission colors were observed only for the compound containing difluorinated benzothiadiazole bonded to two tetraphenylethene. All compounds showed remarkable solvatochromic properties in selected solvents with different polarities. The powder XRD results and mechanochromism of the compounds suggested that the solid state structures can change from one form to another by grinding, fuming or annealing processes.

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Section: Introductionmentioning

confidence: 99%

Synthesis, characterization, aggregation-induced emission, solvatochromism and mechanochromism of fluorinated benzothiadiazole bonded to tetraphenylethenes

Hsu

Weng

2018

RSC Adv.

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“…Hence correlations between different scales based on different indicator molecules have been established. 11,13,19,20 Liquid interfaces, which are the subject of the present study, is a field of intense activity because of the scientific, environmental, and technological importance of interfaces. [21][22][23][24] The asymmetry of the forces at the interface, exemplified by the observation that molecules at liquid surfaces are aligned in a preferential direction rather than randomly oriented as they are in the bulk, 25 is the origin of many of the unique chemical and physical properties of this region.…”

Section: Introductionmentioning

confidence: 99%

Polarity of Liquid Interfaces by Second Harmonic Generation Spectroscopy

1997

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A spectroscopic method, based on the interface selectivity of second-harmonic generation, is used to obtain the polarity of liquid interfaces. In this paper the second-harmonic measurement of the spectrum of the polarity indicator molecule N, N′-diethyl-p-nitroaniline (DEPNA) at the air/water interface demonstrates the method. Two different approaches are used to measure the intramolecular charge transfer (CT) absorption band position of DEPNA at the air/water interface. The DEPNA CT band blue-shifts from 429 nm in bulk water (polar solvent) to 359 nm in bulk hexane (nonpolar solvent) and 329 nm in the gas phase (no solvent). At the air/water interface, the charge transfer peak band maximum occurs at 373 nm, which indicates that the polarity of the air/water interface is similar to those of the bulk solvents carbon tetrachloride and butyl ether. The DEPNA results together with the results from another solvatochromic polarity indicator molecule, ET-(30), which will be reported elsewhere, show that the polarity results of the air/water interface are general.

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“…Varying the difference in dipole moment between the ground and excited states of the chromophore, two different kinds of solvatochromism are possible: a negative solvatochromism corresponds to hypsochromic shift, i.e., blue shift, with increasing solvent polarity; on the other hand, the corresponding bathochromic shift, i.e., red shift, is named positive solvatochromism [39].…”

Section: Uv-visible Spectrophotometry Characterization: a Study Of Somentioning

confidence: 99%

A Combined XRD, Solvatochromic, and Cyclic Voltammetric Study of Poly (3,4-Ethylenedioxythiophene) Doped with Sulfonated Polyarylethersulfones: Towards New Conducting Polymers

et al. 2018

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Despite the poor solubility in organic solvents, poly (3,4-ethylenedioxythiophene) (PEDOT) is one of the most successful conducting polymers. To improve PEDOT conductivity, the dopants commonly used are molecules/polymers carrying sulfonic functionalities. In addition to these species, sulfonated polyarylethersulfone (SPAES), obtained via homogeneous synthesis with different degrees of sulfonation (DS), can be used thanks to both the tight control over the DS and the charge separation present in SPAES structure. Here, PEDOTs having enhanced solubility in the chosen reaction solvents (N,N-dimethylformamide, dimethylacetamide, dimethyl sulfoxide, and N-methyl-2-pyrrolidone) were synthesized via a high-concentration solvent-based emulsion polymerization with very low amounts of SPAES as dopant (1% w/w with respect to EDOT monomer), characterized by different DS. The influence of solvents and of the adopted doping agent was studied on PEDOT_SPAESs analyzing (i) the chemical structure, comparing via X-ray diffraction (XRD) the crystalline structures of undoped and commercial PEDOTs with PEDOT_SPAES' amorphous structure; (ii) solvatochromic behavior, observing UV absorption wavelength variation as solvents and SPAES' DS change; and (iii) electrochemical properties: voltammetric peak heights of PEDOT_SPAES cast onto glassy carbon electrodes differ for each solvent and in general are better than the ones obtained for neat SPAES, PEDOTs, and glassy carbon.

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Solvatochromism and solvent polarity scales

Cited by 281 publications

References 51 publications

Synthesis, characterization, aggregation-induced emission, solvatochromism and mechanochromism of fluorinated benzothiadiazole bonded to tetraphenylethenes

Synthesis, characterization, aggregation-induced emission, solvatochromism and mechanochromism of fluorinated benzothiadiazole bonded to tetraphenylethenes

Polarity of Liquid Interfaces by Second Harmonic Generation Spectroscopy

A Combined XRD, Solvatochromic, and Cyclic Voltammetric Study of Poly (3,4-Ethylenedioxythiophene) Doped with Sulfonated Polyarylethersulfones: Towards New Conducting Polymers

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