Binding properties of 1-pyrenesulfonic acid in water

Menger, Fredric M.; Whitesell, L. G.

doi:10.1021/jo00226a013

Cited by 29 publications

(23 citation statements)

References 7 publications

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“…This behavior may be related to the previously reported dimerization and self-aggregation of PSANa. 38 For comparison absorbances of a micelle forming compound below and above the cmc were recorded. Absorbances of SDS in D20 (see last entry in Table 3) were found to be linear up to -0.1 M (spectra not shown).…”

Section: ([Sj) ( a B S / [ S ] ) Versus Analytical Host Concentratimentioning

confidence: 99%

Near-Infrared Spectroscopic Investigation of Inclusion Complexes between Cyclodextrins and Aromatic Compounds

Politi¹,

Tran²,

Gao³

1995

J. Phys. Chem.

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Near infrared (NIR) absorption in the 900-1800 nm region has been used to characterize and measure the association constants of the inclusion complexes between aromatic compounds (e.g., phenol, 4-chlorophenol, sodium 2-naphthalenesulfonate, and sodium 2-pyrenesulfonate) and a-, B-, and y -cyclodextrin. It was found that the NIR method is particularly suited for this type of study because upon forming complexes, the oscillator strengths of the C-H stretching [Av = 2 (at -1650 nm) and 3 (at -1 120 nm)] overtone bands of the aromatic guest compounds were increased by at least 2-5-fold. The observed increases are rationalized in terms of the enhancement in the anharmonicity and the libration motions of the guest molecule in the CD cavity.This enhancement effect facilitates the calculation of the association constants of the inclusion complexes.As expected, the calculated values are in relatively good agreement with previously determined values.

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Section: ([Sj) ( a B S / [ S ] ) Versus Analytical Host Concentratimentioning

confidence: 99%

Near-Infrared Spectroscopic Investigation of Inclusion Complexes between Cyclodextrins and Aromatic Compounds

Politi¹,

Tran²,

Gao³

1995

J. Phys. Chem.

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“…General methods : All chemicals and solvents were commercially available and used without any purification. The potassium salt of pyrene‐1‐sulfonate was synthesized according to reference to the published procedure 22. The salt was converted to the acid form, 1‐PyS, by passing its aqueous solution through an ion‐exchange column filled with an Amberlite IR 120B NA resin (ORGANO).…”

Section: Methodsmentioning

confidence: 99%

“…The potassium salt of pyrene-1-sulfonate was synthesized according to reference to the published procedure. [22] The salt was converted to the acid form, 1-PyS, by passing its aqueous solution through an ion-exchange column filled with an Amberlite IR 120B NA resin (ORGANO). The organic salts 2 a-c comprising sulfonic acid derivatives and triphenylmethylamine (TPMA) were prepared by mixing of sulfonic acid derivatives and TPMA in a 1:1 molar ratio in methanol.…”

Section: Methodsmentioning

confidence: 99%

Role‐Allocated Combination of Two Types of Hydrogen Bonds towards Constructing a Breathing Diamondoid Porous Organic Salt

Yamamoto

Hasegawa

Hamada

et al. 2013

Chemistry A European J

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A diamondoid porous organic salt (d-POS) composed of 8-hydroxyquinoline-5-sulfonic acid (HQS) and triphenylmethylamine (TPMA) shows reversible structure contraction and expansion ("breathing") in response to guest desorption and adsorption. This flexible structure is designed hierarchically by utilizing two different types of hydrogen bonds. X-ray crystallographic analysis reveals that the two types of hydrogen bonds are formed separately to play respective roles for constructing the d-POS. The strong charge-assisted hydrogen bond between the sulfonate anion of HQS and the ammonium cation of TPMA serves as a static node to provide a supramolecular cluster for a building block. In contrast, the complementary neutral hydrogen bond between the hydroxyl and quinolyl groups of HQS acts as a dynamic linker to connect the clusters. Consequently, these two types of hydrogen bonds yield the d-POS with one-dimensional channels through the formation of diamondoid networks. We clarify that the d-POS undergoes dynamic structure transformation that originates in the cleavage and reformation of the complementary neutral hydrogen bond during guest desorption and adsorption. From the comparative studies, it is also demonstrated that applying the complementary neutral hydrogen bond in the d-POS provides significant advantages in terms of the responsivity of the structure over applying other weak noncovalent interactions for the connection of the clusters. Furthermore, the resultant d-POS also modulates fluorescent profiles dynamically responsive to guest adsorption and desorption.

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“…Firstly, the pyrene-1-sulfonic acid sodium salt (PyS) was synthesized by sulfonating. 20 Then, the as-prepared PyS was further sulfonated by oleum to obtain PTSA. The twostep synthesis method needs lots of separation and purication procedures which would cause environment damage and raw materials waste.…”

Section: Introductionmentioning

confidence: 99%

A facile synthesis of 1,3,6,8-pyrenesulfonic acid tetrasodium salt as a hydrosoluble fluorescent ink for anti-counterfeiting applications

Chen

Zhang

et al. 2019

RSC Adv.

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Binding properties of 1-pyrenesulfonic acid in water

Abstract: Supplementary Material Available: Spectral and analytical data for the addition products (£)-and (Z)-2am, (E)-2bm, (E)-2cm, 2an,ar,bn,bo,br,bs,cr,dr,em,er, and 3 am,an,at,bm,bn,bp,bq,cm,dm,em,frn,gm (8 pages). Ordering information is given on any current masthead page.

Cited by 29 publications

References 7 publications

Near-Infrared Spectroscopic Investigation of Inclusion Complexes between Cyclodextrins and Aromatic Compounds

Near-Infrared Spectroscopic Investigation of Inclusion Complexes between Cyclodextrins and Aromatic Compounds

Role‐Allocated Combination of Two Types of Hydrogen Bonds towards Constructing a Breathing Diamondoid Porous Organic Salt

A facile synthesis of 1,3,6,8-pyrenesulfonic acid tetrasodium salt as a hydrosoluble fluorescent ink for anti-counterfeiting applications

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