Dibutylaminophenyl- and/or Pyridinyl-Capped 2,6,9,10-Tetravinylanthracene Cruciforms: Synthesis and Aggregation-Enhanced One- and Two-Photon Excited Fluorescence

Abstract

This article reports the synthesis, one- and two-photon absorption (2PA), and emission properties of 2,6,9,10-tetraarylvinylanthracene derivatives in both THF solution and aqueous media. The results show that the center-crossed integration of aggregation-induced emission-active 9,10-diarylvinylanthracenes and aggregation-quenched emission-active 2,6-diarylvinylanthracenes does not surely constitute aggregation-enhanced emission (AEE) dyes, and only the dibutylamino-containing cruciforms exhibit AEE effect. The investigation of two-photon properties reveals that the dibutylamino-containing cruciforms show large 2PA cross sections (δmax up to 1500 GM) in both THF solution and THF/water (1/9) mixture, and the two-photon fluorescence action cross sections in aqueous media are about 10 times higher than those in THF solution because of their much higher fluorescence quantum yields in aqueous media. This work has demonstrated that the nature of the building blocks could significantly affect the aggregation behaviors and fluorescence properties of anthracene-centered cruciforms. Cruciforms with excellent 2PA and AEE properties could be constructed by using anthracene as the π-center and suitable aromatic units as building blocks.