Resumen: A set of chiral discotic phenylacetylenes have been synthesized by 3-fold Sonogashira coupling between different ethynylbenzenes and triiodobenzenes. The resultant bulk materials are fully characterized by polarized optical microscopy (POM), differential scanning calorimetry (DSC), and X-ray diffraction. The octopolar nature of the target compounds is studied by UV–vis absorption spectroscopy and hyper-Raleigh scattering in solution. Optimization of the donor–acceptor substitution yields both high hyperpolarizability values and appreciable mesomorphic properties. A simple thin film device for second harmonic generation has been prepared from the nitro-substituted liquid crystalline derivative. Idioma: Inglés DOI: 10.1021/jo302297j Año: 2012 Publicado en: Journal of Organic Chemistry 77, 23 (2012), 10891-10896 ISSN: 0022-3263 Factor impacto JCR: 4.564 (2012) Categ. JCR: CHEMISTRY, ORGANIC rank: 10 / 57 = 0.175 (2012) - Q1 - T1 Financiación: info:eu-repo/grantAgreement/ES/MEC/CTQ2010-1881 Financiación: info:eu-repo/grantAgreement/ES/MEC/MAT2011-27978-C02-01 Tipo y forma: Artículo (PostPrint) Área (Departamento): Área Química Orgánica (Dpto. Química Orgánica)