1111897-49-4Relevant academic research and scientific papers
Sequence-defined dendrons dictate supramolecular cogwheel assembly of dendronized perylene bisimides
Partridge, Benjamin E.,Wang, Li,Sahoo, Dipankar,Olsen, James T.,Leowanawat, Pawaret,Roche, Cecilé,Ferreira, Henrique,Reilly, Kevin J.,Zeng, Xiangbing,Ungar, Goran,Heiney, Paul A.,Graf, Robert,Spiess, Hans W.,Percec, Virgil
, p. 15761 - 15766 (2019)
A dendronized perylene bisimide (PBI) that self-organizes into hexagonal arrays of supramolecular double helices with identical single crystal-like order that disregards chirality was recently reported. A cogwheel model of selfassembly that explains this process was proposed. Accessing the highly ordered cogwheel phase required very slow heating and cooling or extended periods of annealing. Analogous PBIs with linear alkyl chains did not exhibit the cogwheel assembly. Here a library of sequence-defined dendrons containing all possible compositions of linear and racemic alkyl chains was employed to construct self-assembling PBIs. Thermal and structural analysis of their assemblies by differential scanning calorimetry (DSC) and fiber X-ray diffraction (XRD) revealed that the incorporation of n-alkyl chains accelerates the formation of the high order cogwheel phase, rendering the previously invisible phase accessible under standard heating and cooling rates. Small changes to the primary structure, as constitutional isomerism, result in significant changes to macroscopic properties such as melting of the periodic array. This study demonstrated how changes to the sequencedefined primary structure, including the relocation of methyl groups between two constitutional isomers, dictate tertiary and quaternary structure in hierarchical assemblies. This led to the discovery of a sequence that self-organizes the cogwheel assembly much faster than even the corresponding homochiral compounds and demonstrated that defined-sequence, which has long been recognized as determinant for the complex structure of biomacromolecules including proteins and nucleic acids plays the same role also in supramolecular synthetic systems.
Chiral induction by helical neighbour: Spectroscopic visualization of macroscopic-interaction among self-sorted donor and acceptor π-stacks
Molla, Mijanur Rahaman,Das, Anindita,Ghosh, Suhrit
, p. 8934 - 8936 (2011/10/01)
Supramolecular induction of chirality to a π-stacked dialkoxynaphthalene (DAN)-fiber (made of achiral building blocks) from a neighbouring helical naphthalenediimide (NDI)-fiber is reported. CD-studies helped in understanding the nature of co-assembly in the donor-acceptor chromophore mixture from molecular to macroscopic scale.
Control of H- and J-type π stacking by peripheral alkyl chains and self-sorting phenomena in perylene bisimide homo- and heteroaggregates
Ghosh, Suhrit,Li, Xue-Qing,Stepanenko, Vladimir,Wuerthner, Frank
experimental part, p. 11343 - 11357 (2009/10/25)
The synthesis, self-assembly, and gelation ability of a series of organogelators based on perylene bisimide (PBI) dyes containing amide groups at imide positions are reported. The synergetic effect of intermolecular hydrogen bonding among the amide functi
