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Gelation-driven Dynamic Systemic Resolution: in situ Generation and Self-Selection of an Organogelator.

Hu L, Zhang Y, Ramström O - Sci Rep (2015)

Bottom Line: An organogelator was produced and identified from a dynamic imine system, resolved and amplified by selective gelation.The formation of the organogel was monitored in situ by (1)H NMR, showing the existence of multiple reversible reactions operating simultaneously, and the redistribution of the involved species during gelation.The formed organogelator proved effective with a range of organic solvents, including DMSO, toluene, and longer, linear alcohols.

View Article: PubMed Central - PubMed

Affiliation: KTH - Royal Institute of Technology, Department of Chemistry, Teknikringen 30, Stockholm, Sweden.

ABSTRACT
An organogelator was produced and identified from a dynamic imine system, resolved and amplified by selective gelation. The formation of the organogel was monitored in situ by (1)H NMR, showing the existence of multiple reversible reactions operating simultaneously, and the redistribution of the involved species during gelation. The formed organogelator proved effective with a range of organic solvents, including DMSO, toluene, and longer, linear alcohols.

No MeSH data available.


Concept of gelation-driven selection and amplification of organogelator from a thermodynamically controlled dynamic system.A series of substrates Pij is dynamically formed from individual components Aiand Bj, and the dynamic system is subsequently resolved via gel formation of product Pnm.
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f1: Concept of gelation-driven selection and amplification of organogelator from a thermodynamically controlled dynamic system.A series of substrates Pij is dynamically formed from individual components Aiand Bj, and the dynamic system is subsequently resolved via gel formation of product Pnm.

Mentions: Kinetically controlled processes coupled to dynamic systems lead to the concept of dynamic systemic resolution (DSR), in principle enabling kinetic resolution of selected constituents2122. An attractive feature of DSR is the possibility of acquiring complete amplification of the optimal species, regardless of the specific distributions formed in the thermodynamic equilibria, provided the kinetic steps are selective. We have for example shown these features in enzyme-catalyzed selection and asymmetric synthesis of different structures23242526272829, and reported that selective crystallization can be used to control and drive dynamic systems to the amplification of specific constituents3031. In the present study, we expand the concept of DSR to the field of gelation, in which an organic liquid is entrapped in a solid three-dimensional network by capillary forces and adhesion32. Owing to its unique physical properties, increasing attention has been continuously paid to the development of novel organogels, and successful applications have been achieved in fields such as pharmaceutics, cosmetics, food processing, as well as in the oil industry3334. Even though supramolecular hydrogel-based gelation has been used as driving force for component selection3536, the study of organogels remains unexplored. Herein, we report the first example of in situ generation and self-selection of an efficient organogelator at the dynamic constitutional level (Fig. 1).


Gelation-driven Dynamic Systemic Resolution: in situ Generation and Self-Selection of an Organogelator.

Hu L, Zhang Y, Ramström O - Sci Rep (2015)

Concept of gelation-driven selection and amplification of organogelator from a thermodynamically controlled dynamic system.A series of substrates Pij is dynamically formed from individual components Aiand Bj, and the dynamic system is subsequently resolved via gel formation of product Pnm.
© Copyright Policy - open-access
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC4462186&req=5

f1: Concept of gelation-driven selection and amplification of organogelator from a thermodynamically controlled dynamic system.A series of substrates Pij is dynamically formed from individual components Aiand Bj, and the dynamic system is subsequently resolved via gel formation of product Pnm.
Mentions: Kinetically controlled processes coupled to dynamic systems lead to the concept of dynamic systemic resolution (DSR), in principle enabling kinetic resolution of selected constituents2122. An attractive feature of DSR is the possibility of acquiring complete amplification of the optimal species, regardless of the specific distributions formed in the thermodynamic equilibria, provided the kinetic steps are selective. We have for example shown these features in enzyme-catalyzed selection and asymmetric synthesis of different structures23242526272829, and reported that selective crystallization can be used to control and drive dynamic systems to the amplification of specific constituents3031. In the present study, we expand the concept of DSR to the field of gelation, in which an organic liquid is entrapped in a solid three-dimensional network by capillary forces and adhesion32. Owing to its unique physical properties, increasing attention has been continuously paid to the development of novel organogels, and successful applications have been achieved in fields such as pharmaceutics, cosmetics, food processing, as well as in the oil industry3334. Even though supramolecular hydrogel-based gelation has been used as driving force for component selection3536, the study of organogels remains unexplored. Herein, we report the first example of in situ generation and self-selection of an efficient organogelator at the dynamic constitutional level (Fig. 1).

Bottom Line: An organogelator was produced and identified from a dynamic imine system, resolved and amplified by selective gelation.The formation of the organogel was monitored in situ by (1)H NMR, showing the existence of multiple reversible reactions operating simultaneously, and the redistribution of the involved species during gelation.The formed organogelator proved effective with a range of organic solvents, including DMSO, toluene, and longer, linear alcohols.

View Article: PubMed Central - PubMed

Affiliation: KTH - Royal Institute of Technology, Department of Chemistry, Teknikringen 30, Stockholm, Sweden.

ABSTRACT
An organogelator was produced and identified from a dynamic imine system, resolved and amplified by selective gelation. The formation of the organogel was monitored in situ by (1)H NMR, showing the existence of multiple reversible reactions operating simultaneously, and the redistribution of the involved species during gelation. The formed organogelator proved effective with a range of organic solvents, including DMSO, toluene, and longer, linear alcohols.

No MeSH data available.