Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 81, Issue 6, Pages 2581-2588Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.6b00281
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Funding
- Joint Center of Excellence in Integrated Nano Systems (JCIN) at King Abdulaziz City of Science and Technology (KACST) and Northwestern University (NU) [34-944]
- National Science Foundation [DBI-1353682]
- Asian Office of Aerospace RD Grant [FA2386-13-1-4124]
- National Science Foundation under University of Pittsburgh's Grant [DMB-1124131]
- NU
- Center for Bio-Inspired Energy Science, an Energy Frontier Research Center - U.S. Department of Energy, Office of Science, Basic Energy Sciences [DE-SC0000989]
- Direct For Biological Sciences
- Div Of Biological Infrastructure [1353682] Funding Source: National Science Foundation
- Direct For Mathematical & Physical Scien
- Division Of Materials Research [1124131] Funding Source: National Science Foundation
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When equimolar solutions of the enantiomeric naphthalenediimide-based highly rigid triangles R-Delta and S-Delta in ClCH2CH2Cl are mixed, the racemate rac-Delta forms an organogel that is composed of interwoven fibers, resulting from the columnar stacking of the triangles in an alternating R-Delta/S-Delta fashion. Under identical conditions, the pure enantiomers do not form organogels. Density functional theory calculations reveal that the racemic RS dimer is more stable than the RR dimer as a result of the enantiomeric relationship between R-Delta and S-Delta, allowing them to act as two complementary rings comprised of 12 [C-H center dot center dot center dot O] interactions with an unprecedented and uninterrupted circular ADDAADDAADDA.DAADDAADDAAD alignment of hydrogen bond donors (D) and acceptors (A), in contrast with the square wave manner in which the RR dimer forms a complementary yet interrupted ADADAD.DADADA circular sequence of six longer [C-H center dot center dot center dot O] hydrogen bonds. It follows that gelation is favored by weak interactions acting cooperatively in rings under precise stereoelectronic control.
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