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Oligotiofeno 6-mers macrocíclico multifuncional π expandido y oligómeros macrocíclicos relacionados

Masahiko Iyoda¹, Keita Tanaka, Hideyuki Shimizu

¹Department of Chemistry, Graduate School of Science and Engineering, Tokyo Metropolitan University , Hachioji, Tokyo 192-0397, Japan.

Journal of the American Chemical Society

|January 17, 2014

Resumen

Los oligotiofenos macrocíclicos sintetizados exhiben propiedades electrónicas y estructurales únicas. Su polimorfismo permite la fluorescencia sintonizable y la actividad del transistor de efecto de campo (FET), allanando el camino para nuevos materiales electrónicos.

Área de la Ciencia:

Química orgánica es la química orgánica.
Ciencia de los materiales Ciencia de los materiales.
Química supramolecular de las moléculas.

Sus antecedentes:

Los oligotiofenos macrocíclicos son materiales electrónicos orgánicos prometedores.
Comprender sus relaciones estructura-propiedad es crucial para aplicaciones avanzadas.

Objetivo del estudio:

Para sintetizar y caracterizar los oligotiofenos macrocíclicos multifuncionales π expandidos.
Investigar sus propiedades electrónicas, comportamiento de autoensamblaje y potencial para aplicaciones basadas en polimorfismo.

Principales métodos:

Reacción de acoplamiento McMurry para la síntesis.
Bromado-deshidrobromado para la modificación estructural.
Análisis de rayos X y microscopía de túnel de barrido (STM) para estudios estructurales y de autoensamblaje.
Oxidación química para la evaluación de propiedades electrónicas.

Principales resultados:

Síntesis exitosa de 6-, 9-, y 12-mer oligotiofenos y un macrociclo derivado de etileno.
Elucidación de estructuras cristalinas que revelan arquitecturas no planas y de forma redonda.
Formación de redes porosas hexagonales por monocapas autoensambladas del macrociclo de etileno.
Observación de la formación de π-dimero en cationes radicales y comportamientos electrónicos distintos (efectos de corriente de anillo, carácter biradical) en las dications.
Descubrimiento del polimorfismo en el 6-mer oligotiofeno con distintos puntos de fusión y estructuras de estado sólido.

Conclusiones:

Los oligotiofenos macrocíclicos sintetizados muestran diversas características electrónicas y estructurales.
El polimorfismo en el 6-mer permite la conmutación de las propiedades de fluorescencia y transistor de efecto de campo (FET).
Estos materiales tienen potencial para aplicaciones en dispositivos electrónicos avanzados.

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