In this article, the presence and effects of polarizationenhanced hydrogen bonding in 1,8-dihydroxynaphthalene (1,8-DHN) were investigated in detail through a series of experimental and computational studies. First, the conformation of 1,8-DHN, and its ability to make intra-and intermolecular hydrogen bonds were investigated in solid state by X-ray crystallography, in solution by NMR spectroscopy, and computationally by density functional theory. Second, equilibrium binding constants, which were determined by 31 P-NMR titration studies, demonstrated stronger complexation of Ph 3 PO with 1,8-DHN compared to mono-naphthol derivatives 8-methoxy-1naphthol and 1-naphthol. In the final section, 1,8-DHN was observed to be an effective catalyst for the Friedel-Crafts-type addition reaction of indoles to β-nitrostyrenes, and a rationale for this catalytic activity was provided via computational studies. All the findings described in this work support the enhanced hydrogen bond donating ability of 1,8-DHN due to polarization caused by the six-membered intramolecular hydrogen bond present in its structure.
Homoconjugated push–pull chromophores were obtained by an efficient, click-type formal [2+2] cycloadditions. With these short synthetic transformations, complex chromophore structures were achieved in a single step without any by-product formation. Significant second-order optical nonlinearities have been calculated for the synthesized compounds.
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