The synthesis of two novel, water-soluble, sugar-substituted poly(p-phenyleneethynylene)s and their interactions with concanavalin A (Con A) and bacteria (Escherichia coli) are reported, and the issue of sensitivity enhancement is investigated. Both sugar-substituted PPEs (P5 and P7) exhibited strong interactions with Con A with K
SV values exceeding 108 M−1. The binding constants between the sugar-substituted polymers and Con A were also quantitatively calculated using isothermal titration calorimetry (ITC) resulting in association constants as high as 106 M−1. P5 and P7 strongly interact with mannose-binding E. coli, which led to their aggregation.
The structural and electronic consequences of π-π and C-H/π interactions in two alkoxy-substituted 1,8-bis- ((propyloxyphenyl)ethynyl)naphthalenes are explored by using X-ray crystallography and electronic structure computations. The crystal structure of analogue 4, bearing an alkoxy side chain in the 4-position of each of the phenyl rings, adopts a π-stacked geometry, whereas analogue 8, bearing alkoxy groups at both the 2- and the 5-positions of each ring, has a geometry in which the rings are splayed away from a π-stacked arrangement. Symmetry-adapted perturbation theory analysis was performed on the two analogues to evaluate the interactions between the phenylethynyl arms in each molecule in terms of electrostatic, steric, polarization, and London dispersion components. The computations support the expectation that the π-stacked geometry of the alkoxyphenyl units in 4 is simply a consequence of maximizing π-π interactions. However, the splayed geometry of 8 results from a more subtle competition between different noncovalent interactions: this geometry provides a favorable anti-alignment of C-O bond dipoles, and two C-H/π interactions in which hydrogen atoms of the alkyl side chains interact favorably with the π electrons of the other phenyl ring. These favorable interactions overcome competing π-π interactions to give rise to a geometry in which the phenylethynyl substituents are in an offset, unstacked arrangement.
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