Phenolphthalein-Modified β-Cyclodextrin as a Molecule-Responsive Colorless-to-Color Change Indicator

Kuwabara, Tetsuo; Takamura, Makoto; Matsushita, Akiko; Ikeda, Hiroshi; Nakamura, Asao; Ueno, Akihiko; Toda, Fujio

doi:10.1021/jo980613i

Cited by 61 publications

(38 citation statements)

References 24 publications

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“…[1,2] The absorption characteristics of phenolphthaleins included in the b-cyclodextrin cavity change from colorless to purple upon guest binding in alkaline solutions. [2] Thermally stable polymers based on a phenolphthalein backbone such as poly(aryl ether ketone), [3,4] poly(aryl ether sulfone), [5][6][7] and polyarylates exhibit high softening temperature and good solubility characteristics. [8] Recently, phenolphthaleins have also been known to create a photovoltage/ photocurrent when embedded in a photoelectrochemical cell.…”

Section: Introductionmentioning

confidence: 99%

Chemically Amplified Photolithography of a Copolymer Containing Phenolphthalein

Lee

Yuan

Kim

et al. 2003

Macro Chemistry & Physics

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A convenient, low cost micro‐patterning method using a new side group polymer containing phenolphthalein is reported. A random copolymer of t‐BOC‐protected phenolphthalein methacrylate (t‐BMPP) with methyl methacrylate (MMA) was prepared by radical copolymerization in dioxane. The negative‐tone patterns of this polymer could be obtained by photo‐deprotection of the t‐BOC groups due to the effect of dissolution inhibition by the phenolic group of the phenolphthalein. The chemical and optical properties of the polymer were, as anticipated, very close to those of the corresponding phenolphthalein and the pH controlled colorimetric transition was reproducibly observed. The contrast in solubility and chromism upon alkaline treatment makes this polymer a promising candidate for investigating spatially‐directed chromism and selective deposition of pH sensitive polymers.

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Section: Introductionmentioning

confidence: 99%

Chemically Amplified Photolithography of a Copolymer Containing Phenolphthalein

Lee

Yuan

Kim

et al. 2003

Macro Chemistry & Physics

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“…[7,13] The binding between 36TPcCD and guests could be analyzed based on a 1 : 1 host/guest stoichiometry, whereas that for 36TPcCD was fitted to a 2 : 1 stoichiometry, as shown in Figure 5. Binding constants K bind are listed in Table 2.…”

Section: Resultsmentioning

confidence: 99%

“…p-Nitrophenol-modified b-CDs [4,5] exhibit a guest-induced color change from colorless to yellow under neutral conditions, but the change in absorption intensity was small. Phenolphthalein-modified b-CD [6,7] underwent color change from colorless to purple upon guest addition at pH 9.70. As an extension to these studies, we investigated the color-change behavior of two thymolphthalein-modified c-CDs, 65TPcCD and 66TPcCD (Figure 1), which bear a thymolphthalein moiety in the primary hydroxyl side of c-CD.…”

Section: Introductionmentioning

confidence: 99%

“…This mixture (100 mg) was coupled with 3AcCD (194 mg) using dicyclohexylcarbodiimide (DCC) according to a method reported previously. [7] The crude product was purified by column chromatography using an ODS column (Fuji Silysia Chromatorex-ODS-DM1020T) monitoring the absorbance at 260 nm. The fraction containing 35TPcCD was eluted with 50 vol.-% of methanol, followed by the fraction containing 36TPcCD.…”

Section: Introductionmentioning

confidence: 99%

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γ-Cyclodextrin Derivatives Bearing Thymolphthalein Dyes in Their Secondary Hydroxyl Side as Guest-Responsive Color Change Indicators

Yoshida

Ueno

2002

Macromol. Rapid Commun.

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“…CD derivatives can be structurally manipulated by exploiting the appropriate combination of the hydrophobic nature and different sizes of the CD cavity with the specific features of the substituents attached to it. Several CD derivatives have been synthesised and reported with substituents such as amines [3][4][5], amino acids [6-8], peptides [9-11] and aromatic systems [12][13][14]. The chemical modification of CDs offers enormous opportunities, but also challenges for chemists and much effort is being directed to developing new synthetic protocols.…”

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confidence: 99%

Microwave-assisted synthesis of 6-amino-β-cyclodextrins

Puglisi

Spencer

Clarke

et al. 2011

J Incl Phenom Macrocycl Chem

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A general microwave-assisted procedure for the synthesis of 6-amino-b-cyclodextrins is reported. Mono-tosyl-b-cyclodextrin was used as the starting material in a one-pot route employing a solvent-free microwave-assisted reaction with a liquid amine. Shorter reaction times were observed for the formation of 6-aminob-cyclodextrins using this novel microwave approach compared to the thermal procedure.Keywords Microwave-assisted synthesis Á 6-amino-b-cyclodextrins Á Functionalised cyclodextrins Á Mono-pendant cyclodextrins Cyclodextrins (CDs) are extremely appealing for their applications in different fields in both pure and applied chemistry [1,2]. CD derivatives can be structurally manipulated by exploiting the appropriate combination of the hydrophobic nature and different sizes of the CD cavity with the specific features of the substituents attached to it. Several CD derivatives have been synthesised and reported with substituents such as amines [3][4][5], amino acids [6-8], peptides [9-11] and aromatic systems [12][13][14]. The chemical modification of CDs offers enormous opportunities, but also challenges for chemists and much effort is being directed to developing new synthetic protocols.Mono-substitution at the 6-position of b-CD has been reported extensively [15]. In particular, 6-amino-b-CDs can be synthesised from the corresponding liquid amines either by heating [18,19] in an excess of the amine.Herein a general microwave-assisted procedure for the synthesis of a nine-member library of 6-amino-b-CDs (b-CD-X) bonded through nitrogen to C6 carbon of the b-CD is reported. (Figure 1).The use of microwave irradiation (MW) in organic chemistry is becoming increasingly important [20,21]. Nevertheless, only a few papers reporting the use of MW for the modification of CDs have been published [22][23][24][25][26].We report for the first time the synthesis of a library in which liquid amines displaces the tosyl group of the 6-tosyl-b-CD. Our one-pot procedure involves nucleophilic displace of the tosyl group of 6-tosyl-b-CD with liquid amines, or aqueous ammonia solution for 2a, (in a microwave oven at 85°C and 200 W for 30 min) yielding the corresponding mono-substituted amino-CD (b-CD-X). Shorter reaction times were generally found with the MWassisted protocol compared to the thermal procedure.Some of the prepared b-CD-X derivatives have been previously synthesised: 2a [27], 2c [16, 28-30], 2f [31-35], 2g [18].To the best of our knowledge, 2b, 2d, 2e, 2h and 2i are synthesised and characterised for the first time.An excess of liquid amine was reacted with 6-tosyl-b-CD (150:1) in a sealed tube yielding b-CDXs via the MW procedure (30 min, 200 W, 85°C). Microwave reactions were carried out in a CEM Explorer. In the case of 2a aqueous NH 3 solution (28% w/w) was used. Attempts to Electronic supplementary material The online version of this article (

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Phenolphthalein-Modified β-Cyclodextrin as a Molecule-Responsive Colorless-to-Color Change Indicator

Cited by 61 publications

References 24 publications

Chemically Amplified Photolithography of a Copolymer Containing Phenolphthalein

Chemically Amplified Photolithography of a Copolymer Containing Phenolphthalein

γ-Cyclodextrin Derivatives Bearing Thymolphthalein Dyes in Their Secondary Hydroxyl Side as Guest-Responsive Color Change Indicators

Microwave-assisted synthesis of 6-amino-β-cyclodextrins

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