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A síntese de uma plataforma molecular para materiais líquido-cristalinos derivados do ácido 3-arilisoxazolil-5-carboxílico (1) e do 5-(hidroximetil)-3-aril-2-isoxazolina (2) é descrita. Os intermediários 1 e 2 são obtidos através da reação de cicloadição (3+2) 1,3-dipolar entre arilóxidos de nitrilas e os dipolarófilos ácido acrílico e álcool alílico, respectivamente. Os compostos cristais líquidos são sintetizados através de uma estratégia de alongamento molecular do núcleo primitivo isoxazolínico pela conexão de subunidades arilacetilênicas, as quais foram obtidas da reação de Sonogashira. Sob essas condições, séries de cristais líquidos 5a-c, 6, 7a-g e 8a-d têm sido sintetizadas com rendimentos de médios para bons. Os compostos finais apresentam propriedades líquido-cristalinas nematogênica e esmectogênica. Um cálculo DFT no nível B3LYP/6-31G(d,p) é também apresentado e alguns parâmetros estruturais obtidos são analisados. The synthesis of the molecular platform for liquid-crystalline materials based on 3-arylisoxazolyl-5-carboxylic acid (1) and 5-(hydroxymethyl)-3-aryl-2-isoxazoline (2) is described. The key intermediates 1 and 2 are obtained by (3+2) 1,3-dipolar cycloaddition reaction between an arylnitrile oxide and an acrylic acid and allylic alcohol as the dipolarophile. The liquid crystals (LC) compounds are synthesized through a "molecular elongation strategy" from the initial isoxazolinic core by connecting the arylacetylene moiety obtained from the Sonogashira reaction. Under these conditions, the series of liquid crystals 5a-c, 6, 7a-g and 8a-d have been successfully synthesized in fair to good yields. The final compounds display nematic and smectic liquid-crystalline properties. The structural properties of the series of the liquid crystals has been studied using DFT methods at level B3LYP/6-31G(d,p). The equilibrium geometries in the gas phase are presented and analyzed.

3-Arylisoxazolyl-5-carboxylic acid and 5-(Hydroxymethyl)-3-aryl-2-isoxazoline as molecular platforms for liquid-crystalline materials