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231225s2017 xx |||||o 00| ||eng c |
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|a 10.1021/acs.langmuir.7b02191
|2 doi
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|a pubmed24n0919.xml
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|a (DE-627)NLM275972208
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|a (NLM)28926708
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|a DE-627
|b ger
|c DE-627
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|a eng
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|a Singh, Andrew
|e verfasserin
|4 aut
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|a Molecular Nuances Governing the Self-Assembly of 1,3:2,4-Dibenzylidene-d-sorbitol
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|c 2017
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|a Text
|b txt
|2 rdacontent
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|a ƒaComputermedien
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|2 rdamedia
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|a ƒa Online-Ressource
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|2 rdacarrier
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|a Date Completed 30.07.2018
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|a Date Revised 30.07.2018
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|a published: Print-Electronic
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|a Citation Status PubMed-not-MEDLINE
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|a 1,3:2,4-Dibenzylidene-d-sorbitol (DBS) is the gold-standard for low-molecular-weight organogelators (LMOGs). DBS gels a wide array of solvents, as illustrated by the large Hansen sphere representing gels (2δd = 33.5 MPa1/2, δp = 7.5 MPa1/2, and δh = 8.7 MPa1/2; radius = 11.2 MPa1/2). Derivatives of DBS have been synthesized to isolate and determine molecular features essential for organogelation. In this work, π-π stacking and hydrogen bonding are the major noncovalent interactions examined. The importance of π-π stacking was studied using 1,3:2,4 dicyclohexanecarboxylidene-d-sorbitol (DCHS), which eliminates possible π-π stacking while still conserving the other structural aspects of DBS. The replacement of the benzyl groups with cyclohexyl groups led to a very a poor gelator; only one of the several solvents examined, carbon tetrachloride, formed a gel. 1,3:2,4-Diethylidene-d-sorbitol (DES), another DBS analogue incapable of π-π stacking but with very different polarity, gelated a large Hansen space (2δd = 34.0 MPa1/2, δp = 10.9 MPa1/2, and δh = 10.8 MPa1/2; radius = 9.2 MPa1/2). DES gels solvents with higher δp and δh values than DBS. To assess the role of hydrogen bonding, DBS was acetalated (A-DBS), and it was found that the Hansen space gelated by A-DBS shifted to less polar solvents with higher hydrogen-bonding Hansen solubility parameters (HSPs) (2δd = 33.8 MPa1/2, δp = 6.3 MPa1/2, and δh = 9.6 MPa1/2; radius = 11.1 MPa1/2) than for DBS. These systematic structural modifications are the first step in exploring how specific intermolecular features alter aspects of Hansen space corresponding to positive gelation outcomes
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|a Journal Article
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|a Research Support, U.S. Gov't, Non-P.H.S.
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|a Research Support, Non-U.S. Gov't
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| 700 |
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|a Auzanneau, France-Isabelle
|e verfasserin
|4 aut
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| 700 |
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|a Corradini, Maria G
|e verfasserin
|4 aut
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|a Grover, Girishma
|e verfasserin
|4 aut
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|a Weiss, Richard G
|e verfasserin
|4 aut
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| 700 |
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|a Rogers, Michael A
|e verfasserin
|4 aut
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| 773 |
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|i Enthalten in
|t Langmuir : the ACS journal of surfaces and colloids
|d 1992
|g 33(2017), 41 vom: 17. Okt., Seite 10907-10916
|w (DE-627)NLM098181009
|x 1520-5827
|7 nnns
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|g volume:33
|g year:2017
|g number:41
|g day:17
|g month:10
|g pages:10907-10916
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|u http://dx.doi.org/10.1021/acs.langmuir.7b02191
|3 Volltext
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