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Organic & Biomolecular Chemistry Vol -8

Organic & Biomolecular Chemistry Vol -7

Organic & Biomolecular Chemistry Vol -6

Organic & Biomolecular Chemistry Vol -5

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Organic & Biomolecular Chemistry Vol -3

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Conformational polymorphism and amphiphilic properties of resorcinarene octapodands

Content Provider	Royal Society of Chemistry (RSC)
Author	Kurronen, Anni Nauha, Elisa Helttunen, Kaisa Shahgaldian, Patrick Nissinen, Maija
Copyright Year	2011
Abstract	o-Nitroaniline functionalized resorcinarene octapodands 1–5 with pendant methyl, ethyl, pentyl, nonyl or 1-decenyl groups, respectively, were synthesized and their structural properties investigated using X-ray crystallography and NMR spectroscopy. The upper rim of each podand is identical containing flexible side arms, in which rotation around the -OCH2CH2N- linkers create excellent possibilities for polymorphism. Two conformational polymorphs of acetone solvate of 2 were identified containing different side arm orientation and crystal packing. Compound 1 crystallized from acetone and nitromethane yielding two pseudopolymorphs with different packing motifs. The longer alkyl chains of 3–5 lead to differences in solubility and induce amphiphilic properties, which were studied at the air–water interface using the Langmuir-film technique. Crystals of amphiphilic compound 5, which has hydrophobic alkyl tails at the lower rim and hydrophilic nitroaniline groups at the upper rim, showed an interesting packing motif with alternating aromatic and aliphatic layers. Versatile structures of the octapodands in solid state and in solution serve as an example of how conformational flexibility can be utilized in crystal engineering and creating self-assembling monolayer structures.
Starting Page	906
Ending Page	914
Page Count	9
File Format	HTM / HTML PDF
ISSN	14770520
Volume Number	9
Issue Number	3
Journal	Organic & Biomolecular Chemistry
DOI	10.1039/c0ob00602e
Language	English
Publisher	Royal Society of Chemistry
Access Restriction	Open
Subject Keyword	Side arm Crystal engineering Aliphatic compound Resorcinarene Granulocyte Nuclear magnetic resonance spectroscopy Single-nucleotide polymorphism Hydrophobe X-ray crystallography Nitromethane Alkane Amphiphile Hydrophile Acetone
Content Type	Text
Resource Type	Article
Subject	Organic Chemistry Biochemistry Physical and Theoretical Chemistry

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