Crystal Engineering of Acentric Styryl Quinolinium Crystals with Strongly Hydrogen-Bonded Phenolic Anions
Citations Over TimeTop 18% of 2013 papers
Abstract
We report on new acentric styryl quinolinium crystals with phenolic sulfonate counteranions and investigate their supramolecular interactions that affect their quadratic nonlinear optical properties. The phenolic group acting as an electron-donor as well as hydrogen-bond donor site is located at one end of the anion, while the sulfonate group acting as an electron-acceptor as well as hydrogen-bond acceptor site is located at the opposite end of the anion. New styryl quinolinium crystals with 4-hydroxybenzenesulfonate and 6-hydroxynaphthalene-2-sulfonate counteranions exhibit a large macroscopic optical nonlinearity with very efficient second harmonic generation (SHG) efficiency. In styryl quinolinium 4-hydroxybenzenesulfonate crystals, the styryl quinolinium cation chromophores exhibit an acentric ordering with a high order parameter close to 1.0, which is optimal for electro-optic applications or THz-wave generation. The 4-hydroxybenzenesulfonate counteranions form strong head-to-tail hydrogen bonds, and they are also packed in acentric layers. The direction of the polar axes in cation and anion layers is practically identical. Therefore, the introducing phenolic group acting as an electron-donor as well as hydrogen-bond donor to the sulfonate counteranion is a potential technique for crystal engineering to tailor molecular ordering as well as the physical properties of salt-type quinolinium derivatives.
Related Papers
- → Supramolecular chemistry and crystal engineering(2005)31 cited
- → Supramolecular Synthons and Crystal Structure Prediction of Organic Compounds(2004)34 cited
- → The weak hydrogen bond in supramolecular chemistry(2001)6 cited
- → The supramolecular concept as a bridge between organic, inorganic and organometallic crystal chemistry(1996)34 cited
- → The supramolecular concept as a bridge between organic, inorganic and organometallic crystal chemistry(1996)2 cited