Chiral assembly of achiral pseudoisocyanine with D- and L-phenylalanine

Zeng, Lixi; He, Yi; Dai, Zhifeng; Wang, Jian; Wang, Caiqi; Yang, Yonggang

doi:10.1007/s11426-009-0115-y

Cited by 13 publications

(16 citation statements)

References 41 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…55 In this work, the ICD signals of the PAAS-PIC J-aggregates at 560 nm, 532 nm and 499 nm of the optically active PIC J-aggregates that was formed in the anionic polyelectrolyte do not reversed. Moreover, the CD intensity does not show too much change.…”

Section: Chirality Memorization In the Pic-paas J-aggreagatesmentioning

confidence: 66%

“…48,49 The induced optical activity of cyanine dye J-aggregates have been achieved by the induction of large biopolymers such as proteins, 50,51 oligopeptides, 52 polysaccharids, 53 DNA, 54 and small molecules such as amino acids. 55 However, one basic question is still open: exactly how the weak non-covalent interaction among the local chirality of a small molecule translates to global helicity of preferred handedness in supermolecules still remains to be elucidated.…”

Section: Introductionsmentioning

confidence: 99%

See 1 more Smart Citation

Studies on the interaction of achiral cationic pseudoisocyanine with chiral metal complexes

Wang

Zeng

Ding

et al. 2011

Phys. Chem. Chem. Phys.

Self Cite

View full text Add to dashboard Cite

The effect of chiral metal complexes ([Co(en)(3)]I(3)·H(2)O, cis-[CoBr(NH(3))(en)(2)]Br(2), K[Co(edta)]·2H(2)O and [Ru(phen)(3)](PF(6))(2)) on the polymer-bound J-aggregates in aqueous mixtures of pesudoisocyanine (PIC) iodine and poly(acrylic acid, sodium)(PAAS) have been studied by UV-vis absorption, circular dichroism (CD) and fluorescence spectra. At low concentration, the PIC monomers could self-assemble to form supermolecules by binding to each of the COO(-) groups on the polymer chains through electrostatic interactions. After the addition of chiral metal complexes to the formed PIC-PAAS J-aggregates, we found that only the chiral multiple π-conjugated phenanthroline metal complexes could transfer their metal-centered chiral information to the formed J-aggregates. The chiral J-aggregates showed a characteristic induced circular dichroism (ICD) in the visible region of J-band chromophore, and the ICD signals depend on the absolute configuration, concentration of the chiral multiple π-conjugated metal complexes, as well as temperature. More interestingly, the supramolecular chirality of the polymer supported PIC J-aggregates could be memorized even after the addition of an excess opposite chiral complex enantiomers. This is in sharp contrast to the behavior in the high concentrated NaCl induced PIC-J aggregates, in which the optical rotation of a mixture of two enantiomers varies linearly with their ratio.

show abstract

Section: Chirality Memorization In the Pic-paas J-aggreagatesmentioning

confidence: 66%

Section: Introductionsmentioning

confidence: 99%

Studies on the interaction of achiral cationic pseudoisocyanine with chiral metal complexes

Wang

Zeng

Ding

et al. 2011

Phys. Chem. Chem. Phys.

Self Cite

View full text Add to dashboard Cite

show abstract

“…He et al 36 established a chirality-sensing system based on pseudoisocyanine (PIC, 38) aggregates. Achiral PIC 38 is known to form J-type aggregates, with its critical aggregation concentration in water tuneable by salt concentration.…”

Section: Supramolecular Polymersmentioning

confidence: 99%

Optical chirality sensing using macrocycles, synthetic and supramolecular oligomers/polymers, and nanoparticle based sensors

et al. 2015

View full text Add to dashboard Cite

Optical sensors that respond to enantiomeric excess of chiral analytes are highly demanded in chirality related research fields and demonstrate their potential in many applications, for example, screening of asymmetric reaction products. Most sensors developed so far are small molecules. This Tutorial Review covers recent advances in chirality sensing systems that are different from the traditional small molecule-based sensors, by using macrocycles, synthetic oligomers/polymers, supramolecular polymers and nanoparticles as the sensors, in which supramolecular interactions operate.

show abstract

“…A number of researchers have revealed that some small achiral molecules can form chiral nano/micro-structures by host-guest and guest-guest interactions. [28][29][30][31][32][33][34][35][36][37][38][39][40] The driving force for the formation of chiral supermolecules is generally constructed on the non-covalent interactions, such as van der Waals interactions, hydrogen bonds, p-p stacking, metal coordination, electrostatic interaction and hydrophobic interactions.…”

Section: Introductionmentioning

confidence: 99%

Aggregation of an anionic porphyrin with chiral metal complexes and the competitive binding influences of a surfactant and a polyelectrolyte

et al. 2011

Self Cite

View full text Add to dashboard Cite

The non-covalent interactions of chiral metal complexes with the achiral 5,10,15,20-tetrakis (4-sulonatophenyl) porphyrin (H(4)TTPS(2-)) have been investigated by UV-vis and circular dichroism (CD) spectra. The results show that under acidic environments, only the chiral complex cations ([CoBr(NH(3))(en)(2)](+), [Co(en)(3)](3+), [Ru(phen)(3)](2+)) could interact with H(4)TTPS(2-) to form chiral aggregates, accompanied with the metal-centered chirality information transferred to the formed J-aggregates. However, the chiral complex anion ([Co(edta)](-)) does not cause the self-assembly process. The competitive binding interactions between an achiral water-soluble cationic surfactant (N-hexadecyltrimethyl ammonium chloride, CTAC) and a cationic polyelectrolyte (polyallylamine, PAA) with the chiral metal complex H(4)TTPS(2-) J-aggregates, respectively, were also investigated. It was found that chiral-symmetry-breaking phenomena occur in the cationic surfactant induced event. In the case of a cationic polyelectrolyte, it could change the conformational flexibility of the H(4)TTPS(2-) aggregates. These results may lead us to understand the possible mechanism of the supramolecular self-assembly process by the non-covalent interactions.National Natural Science Foundation of China[20973136, 20877099, 20972183]; State Key Laboratory of Natural and Biomimetic Drugs[20080208]; Hunan High Education Research Fund[06C068]; GUCAS (A B); Ministry of Science and Technology of China[2008AA100801]; Guangdong Province[2010B090300031]; CAS[2010B090300031

show abstract

Chiral assembly of achiral pseudoisocyanine with D- and L-phenylalanine

Cited by 13 publications

References 41 publications

Studies on the interaction of achiral cationic pseudoisocyanine with chiral metal complexes

Studies on the interaction of achiral cationic pseudoisocyanine with chiral metal complexes

Optical chirality sensing using macrocycles, synthetic and supramolecular oligomers/polymers, and nanoparticle based sensors

Aggregation of an anionic porphyrin with chiral metal complexes and the competitive binding influences of a surfactant and a polyelectrolyte

Contact Info

Product

Resources

About