Two-photon absorption and mechanofluorochromic properties of 1,4-diketo-2,5-dibutyl-3,6-bis(4-(carbazol-N-yl)phenyl)pyrrolo[3,4-c]pyrrole

• Published in: Journal of luminescence Vol. 194; pp. 588 - 593
• Main Authors: Zhang, Kai, Chen, Mingshuai, Liu, Zhongwei, Ying, Shian, Zhang, Haichang, Xue, Shanfeng, Yang, Wenjun
• Format: Journal Article
• Language: English
• Published: Elsevier B.V 01.02.2018
• Subjects: D-π-D molecule; Fluorescent DPP derivative; Mechanochromic luminescence; Multifunctional dye; Two-photon absorption; Two-photon absorption; Mechanochromic luminescence; Fluorescent DPP derivative; D-π-D molecule; Multifunctional dye
• ISSN: 0022-2313; 1872-7883
• DOI: 10.1016/j.jlumin.2017.09.018

A new diketopyrrolopyrrole-based fluorescent dye 1,4-diketo-2,5-dibutyl-3,6-bis(4- (carbazol-N-yl)phenyl)pyrrolo[3,4-c]pyrrole (DPPCZ) was synthesized and characterized. DPPCZ with donor–π–acceptor–π–donor motif exhibited large and solvent-dependent two-photon absorption cross sections (δ) and emitted strong two-photon excitation fluorescence. The measured maximal δ values in CHCl3, THF, DMF, and toluene are 750, 610, 600, and 460g, respectively. While DPPCZ water-dispersions exhibit aggregation-quenched emission to some extent, the pristine powder, the obtained single crystal, and emulsion could still emit the relatively strong fluorescence with the efficiency of 21%, 9.5%, and 24%, respectively. It was found that both yellow and red DPPCZ crystals with weak intermolecular interactions could be ground into an amorphous orange state, and then recovered to the yellow state by thermal annealing and solvent-fuming, affording a new DPP-based mechanofluoro-chromic (MFC) material. Powder X-ray diffraction and differential scanning calorimetry indicated that the phase transition between crystalline and amorphous states upon external stimuli was responsible for the MFC behavior. [Display omitted] •A new 1,4-diketo-pyrrolo[3,4-c]pyrrole derivative (DPPCZ) is synthesized.•Fluorescent DPPCZ exhibits large and solvent-dependent 2PA cross sections.•DPPCZ shows two crystalline states and obvious mechanofluorochromism.