New polyaromatic molecular tubes with a subnanometer pore (0.8 nm) were prepared. The tube bearing six sulfonate groups on the periphery and twelve methoxy groups at the openings provides a cylindrical hydrophobic cavity with a length of ∼1.3 nm. The aqueous tube can quantitatively bind one molecule of hydrocarbon guests in water with accompanying guest-induced emission enhancement (up to ∼3 times) of the host framework.
A polyaromatic tube with a subnanometer-sized cavity was efficiently prepared on a gram-scale through the stereo-controlled cyclotrimerization of a diphenylanthracene derivative as a key step. The facile exterior alkylation of the polyaromatic framework leads to a moderately fluorescent tube (R=-OC H ; Φ =20 %) in the solid state. The emission intensity of the solid-state alkyl-substituted tube is remarkably enhanced upon heating (up to 1.6 times, Φ =31 %) as well as doping with fluorescent dyes (up to 4.2 times, Φ =83 %) through efficient energy transfer.
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