Mesitylboron-substituted ladder-type pentaphenylenes: charge-transfer, electronic communication, and sensing properties

Journal of the American Chemical Society
Gang ZhouKlaus Müllen

Abstract

A series of dimesitylboron (B)- or ditolylamino (N)-substituted ladder-type pentaphenylenes (PP) has been designed and synthesized. The UV-vis absorption spectra of compounds BPPN, BPPB, and NPPN reveal an identical maximum wavelength at 432 nm, which indicates that the B and N centers have very similar contributions to the extended conjugation. A rather weak solvatochromism in the UV-vis absorption spectra is observed for compound BPPN, while a remarkable solvatochromic emission is achieved even though the distance between the B and the N centers is as huge as 22 A. The photoluminescence of BPPN shows a bathochromic shift of 108 nm when the solvent polarity is increased from cyclohexane (453 nm) to acetone (561 nm). Compound BPPN acts as a colorimetric and fluorescent chemosensor with high sensitivity (10(-5) M) and selectivity for F(-) over other halogen ions. By inhibiting the charge transfer (CT) from the N center to the B center, the intense green CT emission of compound BPPN rapidly switches into the sky-blue emission of PP when F(-) is bound to the B center. Furthermore, a CT emission can be switched "on" and "off" when compound BPPB is used as F(-) sensory material. Such an intramolecular CT emission between the two B c...Continue Reading

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