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Oligomeric Tectonics: Supramolecular Assembly of Double‐Stranded Oligobisnorbornene through π–π Stacking
Author(s) -
Lee ShernLong,
Lin NaiTi,
Liao WeiChih,
Chen Chunhsien,
Yang HsiaoChing,
Luh TienYau
Publication year - 2009
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200901634
Subject(s) - stacking , supramolecular chemistry , materials science , chemical physics , dynamic light scattering , dipole , molecular dynamics , self assembly , scanning tunneling microscope , scattering , side chain , nanotechnology , crystallography , polymer , chemistry , computational chemistry , optics , physics , nanoparticle , composite material , organic chemistry , crystal structure
Self‐assembly at the molecular level in solutions or on a surface is a subject of current interest. Herein we describe the tailoring of oligobisnorbornene 1 , which represents an innovative concept of a preorganized building block on the tens of nanometer scale. The rodlike 1 has vinyl and styrenyl end groups. Scanning tunneling microscopy (STM) reveals that the oligomers aggregate anisotropically along the long axis and form a one‐dimensional assembly in which, remarkably, no interstitial gap appears between neighboring oligomers. Dynamic light‐scattering (DLS) measurements indicate that the assembly develops in solution. With a shear treatment for dropcast films, a unidirectionally ordered domain with a defect density less than 0.5 % can be prepared. Simulation results by molecular dynamics suggest that there may be multiple interactions such as π–π stacking and dipolar attractions taking place between the termini of the oligomers. To demonstrate the importance of double bonds in the oligomeric backbones and termini towards the tectonic assembly, a hydrogenated analogue was synthesized; π–π interactions are thus less significant and the film morphology is completely different from that of 1 . This work extends the concept of molecular tectonics to preorganized oligomers and opens up a new avenue of nanopatterning toward nanodevices.