A turn-on type stimuli-responsive fluorescent dye with specific solvent effect: Implication for a new prototype of paper using water as the ink

Xiaochen Hu; Yang Liu; Yuai Duan; Jingqi Han; Zhongfeng Li; Tianyu Han

doi:10.1016/j.saa.2017.04.079

A turn-on type stimuli-responsive fluorescent dye with specific solvent effect: Implication for a new prototype of paper using water as the ink

Spectrochim Acta A Mol Biomol Spectrosc. 2017 Sep 5:184:7-12. doi: 10.1016/j.saa.2017.04.079. Epub 2017 Apr 29.

Authors

Xiaochen Hu¹, Yang Liu², Yuai Duan¹, Jingqi Han¹, Zhongfeng Li¹, Tianyu Han³

Affiliations

¹ Department of Chemistry, Capital Normal University, 100048 Beijing, P.R. China.
² Beijing Key Laboratory of Radiation Advanced Materials, Beijing Research Center for Radiation Application, 100015 Beijing, P.R. China.
³ Department of Chemistry, Capital Normal University, 100048 Beijing, P.R. China. Electronic address: phanw@163.com.

PMID: 28475959
DOI: 10.1016/j.saa.2017.04.079

Abstract

In this study, we reported the photoluminescence (PL) behaviour of a new intramolecular charge transfer (ICT) compound, ((E)-2-(((2-hydroxynaphthalen-1-yl)methylene)amino)benzoic acid, (HABA), which shows ICT solvent effect in aprotic solvents as confirmed by absorption and emission spectra. While in protic solvents including water and ethanol, the charge transfer (CT) band significantly reduces. Remarkable fluorescence enhancement in the blue region was also observed for HABA in polar protic solvents. We described such phenomena as "specific solvent effect". It can be ascribed to the hydrogen bonding formation between HABA and protic solvents, which not only causes significant reduction in the rate of internal conversion but also elevates the energy gap. Density functional theory (DFT) calculations as well as the dynamics analysis were performed to further verify the existence of hydrogen bonding complexes. Stronger emission turn-on effect was observed on HABA solid film when it is treated with water and base solution. The stimuli-responsive fluorescence of HABA enables a new green printing technique that uses water/base as the ink, affording fluorescent handwritings highly distinct from the background. Thermoanalysis of the dye suggests the nice thermostability, which is highly desired for real-world printing in a wide temperature range.

Keywords: Fluorescent dye; Paper; Solvent effect; Water-based ink; Water-sensitive.