Abstract
We have designed two rod-shaped compounds each incorporating a naphthalene diimide core and two terminal carboxylic acids. Both molecules aggregate in aqueous solution and spontaneously organize into cylindrical microstructures on the surface of solid substrates. Presumably, hydrogen bonds between the carboxylic acid termini and hydrophobic contacts between the naphthalene diimide cores are mainly responsible for the formation of these supramolecular arrays. Indeed, extended stacks of molecules self-assemble with close contacts between their aromatic cores in single crystals grown from polar solvents.
| Original language | English |
|---|---|
| Pages (from-to) | 5695-5698 |
| Number of pages | 4 |
| Journal | Tetrahedron Letters |
| Volume | 46 |
| Issue number | 34 |
| DOIs | |
| State | Published - Aug 22 2005 |
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Keywords
- Bolaamphiphiles
- Hydrogen bonding
- Hydrophobic interactions
- Naphthalene diimides
- Self-assembly
- Supramolecular arrays
ASJC Scopus subject areas
- Biochemistry
- Organic Chemistry
- Drug Discovery
Cite this
Self-assembly of naphthalene diimides into cylindrical microstructures. / Tomasulo, Massimiliano; Naistat, David M.; White, Andrew J P; Williams, David J.; Raymo, Francisco.
In: Tetrahedron Letters, Vol. 46, No. 34, 22.08.2005, p. 5695-5698.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Self-assembly of naphthalene diimides into cylindrical microstructures
AU - Tomasulo, Massimiliano
AU - Naistat, David M.
AU - White, Andrew J P
AU - Williams, David J.
AU - Raymo, Francisco
PY - 2005/8/22
Y1 - 2005/8/22
N2 - We have designed two rod-shaped compounds each incorporating a naphthalene diimide core and two terminal carboxylic acids. Both molecules aggregate in aqueous solution and spontaneously organize into cylindrical microstructures on the surface of solid substrates. Presumably, hydrogen bonds between the carboxylic acid termini and hydrophobic contacts between the naphthalene diimide cores are mainly responsible for the formation of these supramolecular arrays. Indeed, extended stacks of molecules self-assemble with close contacts between their aromatic cores in single crystals grown from polar solvents.
AB - We have designed two rod-shaped compounds each incorporating a naphthalene diimide core and two terminal carboxylic acids. Both molecules aggregate in aqueous solution and spontaneously organize into cylindrical microstructures on the surface of solid substrates. Presumably, hydrogen bonds between the carboxylic acid termini and hydrophobic contacts between the naphthalene diimide cores are mainly responsible for the formation of these supramolecular arrays. Indeed, extended stacks of molecules self-assemble with close contacts between their aromatic cores in single crystals grown from polar solvents.
KW - Bolaamphiphiles
KW - Hydrogen bonding
KW - Hydrophobic interactions
KW - Naphthalene diimides
KW - Self-assembly
KW - Supramolecular arrays
UR - http://www.scopus.com/inward/record.url?scp=22544466970&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=22544466970&partnerID=8YFLogxK
U2 - 10.1016/j.tetlet.2005.06.086
DO - 10.1016/j.tetlet.2005.06.086
M3 - Article
AN - SCOPUS:22544466970
VL - 46
SP - 5695
EP - 5698
JO - Tetrahedron Letters
JF - Tetrahedron Letters
SN - 0040-4039
IS - 34
ER -