Structure and dynamics of pyrimidine-based macrocycles in solution

Kozlov, A. V.; Семенов, В. Э.; Mikhailov, A. S.; Резник, В. С.; Latypov, Shamil K.

doi:10.1016/j.tetlet.2008.09.047

Cited by 3 publications

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“…In addition, the formation of the hydrogen bond network is rather expected with the uracil and thiocytosin fragments involved. It was reported based on IR spectroscopy , and NMR spectroscopy data that macrocycles consisting of two thiocytosine and one uracil moieties with the same structure as pyrimidinophane 1 form intra- and intermolecular hydrogen bonds in chloroform solutions via NH of thiocytosines as H-donors and CO of uracil as H-acceptor. The same H-bonds can occur in solutions of the pyrimidinophanes with onium fragments in particular bola B1 .…”

Section: Resultsmentioning

confidence: 99%

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Novel Bolaamphiphilic Pyrimidinophane As Building Block for Design of Nanosized Supramolecular Systems with Concentration-Dependent Structural Behavior

Voronin

Gabdrakhmanov

Семенов

et al. 2011

ACS Appl. Mater. Interfaces

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A new macrocyclic bolaamphiphile with thiocytosine fragments in the molecule (B1) has been synthesized and advanced as perspective platform for the design of soft supramolecular systems. Strong concentration-dependent structural behavior is observed in the water-DMF (20% vol) solution of B1 as revealed by methods of tensiometry, conductometry, dynamic light scattering, and atomic force microscopy. Two breakpoints are observed in the surface tension isotherms. The first one, around 0.002 M, is identified as a critical micelle concentration (cmc), whereas the second critical concentration of 0.01 M is a turning point between the two models of the association involved. Large aggregates of ca. 200 nm are mostly formed beyond the cmc, whereas small micelle-like aggregates exist above 0.01 M. The growth of aggregates between these critical points occurs, resulting in a gel-like behavior. An unusual decrease in the solution pH with concentration takes place, which is assumed to originate from the steric hindrance around the B1 head groups. Because of controllable structural behavior, B1 is assumed to be a candidate for the development of biomimetic catalysts, nanocontainers, drug and gene carriers, etc.

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Section: Resultsmentioning

confidence: 99%

“…This procedure was repeated 5 times, and the oily product was dried under reduced pressure. Found: C, 60…”

Section: Bolaamphiphilic Pyrimidinophane B1mentioning

confidence: 99%