The Open Organic Chemistry Journal

2009, 3 : 11-21
Published online 2009 January 26. DOI: 10.2174/1874095200903010011
Publisher ID: TOOCJ-3-11

Synthesis of Pyrene-Anthracene Conjugated Molecular Rods

J.G. Domínguez Chávez , S. Hernandez Ortega and M. Martínez-García
Instituto de Química, Universidad Nacional Autónoma de México, Cd. Universitaria, Coyoacán, C.P. 04510, México D.F., México

ABSTRACT

Fully conjugated pyrene-anthracene-based molecular rods were synthesized by the Horner-Wadsworth– Emmons reaction utilizing potassium tert-butoxide in dry THF. The synthesized rods, which have butylene groups as solubility spacers in the main chain, exhibited good solubility in polar solvents. The solutions of the synthesized pyrenecontaining molecular rods exhibited a blue shift in the UV-vis from the absorption maximum due to the presence of the pyrene group in comparison with the dialdehydes. The chemical structure and purity of the synthesized rods were confirmed by 1H and 13C NMR, FAB+, MALDI-TOF, electrospray mass spectra and elemental analysis.

Keywords:

Molecular rods, Horner-Wadsworth–Emmons, anthracene, pyrene.