Aggregation-Induced Emission and Large Two-Photon Absorption Cross-Sections of Diketopyrrolopyrrole (DPP) Derivatives
Bing Wang A , Nannan He A , Bo Li B , Shuangying Jiang C , Yi Qu A , Sanyin Qu A and Jianli Hua A D
+ Author Affiliations
- Author Affiliations
A Key Laboratory for Advanced Materials, Institute of Fine Chemicals and Department of Chemistry, East China University of Science and Technology, 130 Meilong Road, Shanghai 200237, P. R. China.
B Key Laboratory of Polar Materials and Devices, Ministry of Education, East China Normal University, Shanghai 200241, P. R. China.
C School of Environmental Science and Engineering, Tongji University, Shanghai 200092, P. R. China.
D Corresponding author. Email: jlhua@ecust.edu.cn
Australian Journal of Chemistry 65(4) 387-394 https://doi.org/10.1071/CH11410
Submitted: 22 October 2011 Accepted: 19 February 2012 Published: 27 March 2012
Abstract
In this work, a new series of triphenylamine-based diketo-pyrrolo-pyrrole (DPP) compounds (DPP-I, DPP-II, DPP-III) have been designed and synthesized by a concise route. Their one- and two-photon absorption properties have been investigated. It was found that DPP-based compounds are very weakly fluorescent in THF solution, but their intensities are increased by almost 29, 9, and 24 times in water/THF (v/v 90 %) mixtures, respectively, in which they exhibit a strongly enhanced red fluorescence. The result indicates that the intramolecular vibration and rotation of these dyes is considerably restricted in nano-aggregates formed in water/THF mixtures, which leads to significant increases in fluorescence. The two-photon absorption (2PA) cross-sections measured by the open aperture Z-scan technique were determined to be 188, 275 and 447 GM for DPP-I, DPP-II, and DPP-III, respectively; DPP-III with the symmetrical structure shows the highest value of 2PA cross-section. The excellent properties of aggregation-induced emission (AIE) and 2PA provide an attractive alternative for the biophotonic materials.
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