Proton-Triggered Hypsochromic Luminescence in 1,1'-(2,5-Distyryl-1,4-phenylene) Dipiperidine

Jinlong Chen; Suqian Ma; Jibo Zhang; Lijuan Wang; Ling Ye; Bao Li; Bin Xu; Wenjing Tian

doi:10.1021/jz501383d

Proton-Triggered Hypsochromic Luminescence in 1,1'-(2,5-Distyryl-1,4-phenylene) Dipiperidine

J Phys Chem Lett. 2014 Aug 21;5(16):2781-4. doi: 10.1021/jz501383d. Epub 2014 Jul 31.

Authors

Jinlong Chen¹, Suqian Ma¹, Jibo Zhang¹, Lijuan Wang¹, Ling Ye¹, Bao Li¹, Bin Xu¹, Wenjing Tian¹

Affiliation

¹ State Key Laboratory of Supramolecular Structure and Materials, Jilin Unversity, Qianjin Street No. 2699, Changchun 130012, People's Republic of China.

PMID: 26278078
DOI: 10.1021/jz501383d

Abstract

A proton-triggered hypsochromic luminescent chromophore 1,1'-(2,5-distyryl-1,4-phenylene) dipiperidine (DPD) was designed and synthesized. Upon treatment by hydrochloric acid (HCl), the emission of DPD showed a large hypsochromic shift in both THF solution and microcrystals. Theoretical calculations and powder X-ray diffraction experiments reveal that the switchable emission of DPD originated from the change of the distribution and the spatial arrangement of the frontier molecular orbitals, and the different stacking modes of DPD in microcrystals also contribute to the switchable emission of DPD in aggregates.

Keywords: acid/base stimuli; aggregating structure; frontier molecular orbitals; stacking mode; switchable fluorescent emission.