17088-22-1Relevant articles and documents
Binding Sites of Pyrene and Related Compounds and Chiral Excimer Formation in the Cavities of Cyclodextrins and Branched Cyclodextrins
Kano, Koji,Matsumoto, Hitoshi,Yoshimura, Yoshimichi,Hashimoto, Shizunobu
, p. 204 - 209 (1988)
Circular dicroism (CD) and circularly polarized fluorescence (CPF) spectra reveal the formation of the intermolecular dimer of pyrene having left-handed chirality and intramolecular dimers of 1,3-dinaphtylpropanes having right-handed chiralities in the γ-cyclodextrin cavity.These guest molecules are estimated to be bound to the relatively hydrophobic primary hydroxyl group side of the γ-cyclodextrin cavity, while the more hydrophilic secondary hydroxyl group side is the binding site of the chiral pyrene dimer in the 6-O-α-maltosyl-γ-cyclodextrin cavity because the narrower side of the cavity is capped by the maltosyl group.The pyrene dimer in the branched γ-cyclodextrin exhibits right-handed chirality.
Pyrene-sensitized electron transport across vesicle bilayers: Dependence of transport efficiency on pyrene substituents
Mizushima, Tadashi,Yoshida, Asako,Harada, Akitomo,Yoneda, Yu,Minatani, Tomiaki,Murata, Shigeru
, p. 4336 - 4344 (2008/09/19)
Endoergic electron transport across vesicle bilayers from ascorbate (Asc-) in the inner waterpool to methylviologen (MV2+) in the outer aqueous solution was driven by the irradiation of pyrene derivatives embedded in the vesicle bilayers. The initial rate of MV2+ reduction is dependent on the substituent group of the pyrenyl ring; a hydrophilic functional group linked with the pyrenyl ring by a short methylene chain acts as a sensitizer for the electron transport. Mechanistic studies using (1-pyrenyl)alkanoic acids (1a-c) as sensitizers suggest that the electron transport is mainly initiated by the reductive quenching of the singlet excited state of the pyrene by Asc- and proceeds by a mechanism involving electron exchange between the pyrenes located at the inner and outer interface across the vesicle bilayer. We designed and synthesized novel unsymmetrically substituted pyrenes having both a hydrophilic group linked by a short methylene chain and a hydrophobic long alkyl group (5a-c), which acted as excellent sensitizers for the electron transport across vesicle bilayers. The Royal Society of Chemistry 2006.
Pyrene-derived novel one- and two-component organogelators
Babu,Sangeetha,Vijaykumar,Maitra, Uday,Rissanen, Kari,Raju
, p. 1922 - 1932 (2007/10/03)
A new class of alkyl-chainappended pyrene derivatives 4 - 14 were synthesized and evaluated for their gelation abilities. Depending on the nature of the linking group, these compounds gelated a number of organic solvents, either in the presence or in the absence of the acceptor molecule 2,4,7-trinitrofluorenone (TNF). Compounds with ester, ether, or alkyl linkages gelated a number of hydroxylic and hydrocarbon solvents by means of a charge-transfer interaction with TNF, while compounds with amide, urethane and urea linkers formed gels on their own in a variety of solvents by means of π-π stacking and hydrogen-bonding interactions. The X-ray crystal structure of urethane (S)-12 showed hydrogen-bonding and stacking features, as suggested by the model. The gels obtained were investigated by spectroscopic and electron microscopic techniques which provided structural insights.
Laser Photolysis Studies on the Intramolecular Dimer Radical Cations Formed in 1,3-Dipyrenylpropanes
Tsuchida, Akira,Tsujii, Yoshinobu,Ohoka, Masataka,Yamamoto, Masahide
, p. 5797 - 5802 (2007/10/02)
The structure and stabilization energy of dimer radical cations of intramolecular and intermolecular pyrenyl compounds were estimated by nanosecond laser photolysis in visible and near-IR regions.Electron-transfer quenching of three intramolecular dipyrenyl compounds, 1,3-di(1-pyrenyl)propane (1Py1Py), 1-(1-pyrenyl)-3-(2-pyrenyl)propane (1Py2Py), and 1,3-di(2-pyrenyl)propane (2Py2Py), produced the intramolecular dimer radical cation in an acetonitrile solution.The charge resonance (CR) band of dimer radical cations of 1Py1Py and 2Py2Py was located at 1600 nm, and this structure was ascribed to the full-overlap conformation of two pyrenyl groups.On the other hand, 1Py2Py formed a partial-overlap dimer cation radical whose CR band appeared at >2200 nm, which indicates a stability of ca. 2.4 kcal mol-1 less than that of the full-overlap type.The intermolecular pyrene (Py) dimer radical cation had a CR band at 1450-nm peak and was ca. 0.9 kcal mol-1 more stable than the full-overlap structure of 1Py1Py and 2Py2Py dimer radical cations.This conformation of intermolecular Py dimer radical cations was ascribed to a distorted conformation.
