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    Polarization-Enhanced Hydrogen Bonding in 1,8-Dihydroxynaphthalene: Conformational Analysis, Binding Studies and Hydrogen Bonding Catalysis
    (Wiley-V C H Verlag Gmbh, 2020) Mammadova, Flora; Hamarat, Busra; Ahmadli, Dilgam; Sahin, Onur; Bozkaya, Ugur; Turkmen, Yunus E.
    In this article, the presence and effects of polarization-enhanced 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 P-31-NMR titration studies, demonstrated stronger complexation of Ph3PO with 1,8-DHN compared to mono-naphthol derivatives 8-methoxy-1-naphthol 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 beta-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.
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    Rapid Access to Hydroxyfluoranthenes via a Domino Suzuki-Miyaura/Intramolecular Diels-Alder/Ring-Opening Reactions Sequence
    (Amer Chemical Soc, 2022) Ahmadli, Dilgam; Sahin, Yesim; Calikyilmaz, Eylul; Sahin, Onur; Turkmen, Yunus E.
    In this work, we developed an efficient method for the rapid construction of fluoranthene skeleton to access a variety of substituted hydroxyfluoranthenes. The 1-iodo-8-alkynylnaphthalene derivatives, which serve as substrates for the key fluoranthene-forming step, were prepared via selective monoalkynylative Sonogashira reactions of 1,8-diiodonaphthalene. The domino reaction sequence which involves a sequential Suzuki-Miyaura coupling, an intramolecular Diels-Alder reaction, and an aromatization-driven ring-opening isomerization has been shown to give substituted hydroxyfluoranthenes in up to 92% yield. This work demonstrates the utility of designing new domino reactions for rapid access to substituted polycyclic aromatic hydrocarbons (PAHs).