Alkylation-, Heating-, and Doping-Induced Emission Enhancement of a Polyaromatic Tube in the Solid State.

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=-OC10 H21 ; ΦF =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, ΦF =31 %) as well as doping with fluorescent dyes (up to 4.2 times, ΦF =83 %) through efficient energy transfer.