Chiral Dual Core Chromophores Based on Binaphthyl Acrylonitrile Motif with Tunable Dual Emission Bands and Anti‐counterfeiting

Author:

Qu Jun1,Zhang Qing1,Liao Xiaoming2,Song Cunyu1,Meng Xin1,He Yuanchun1,Li Zan1,Zhang Xiaoxiang2,Cao Ziping1ORCID

Affiliation:

1. Shandong Key Laboratory of Life-Organic Analysis Key Laboratory of Pharmaceutical Intermediates and Analysis of Natural Medicine School of Chemistry and Chemical Engineering Qufu Normal University Qufu 273165 Shandong P. R. China

2. College of Chemical Engineering Nanjing Forestry University Nanjing 210037 P. R. China

Abstract

AbstractSmall organic molecules which can emit fluorescence with tunable dual emission bands are significant for fundamental research and broad applications. In this work, two binaphthyl based arylacrylonitrile derivatives with pyrene and triphenylamine unit (BiNpPy and BiNpTPA) were designed and synthesized, respectively, featuring chiral backbone and dual AIE‐active cyanostyrene‐linked chromophores. Excellent fluorescence emissions in a range of solution and solid states were observed with high quantum yields, indicative of the solvatochromism and mechanochromism. More interestingly, dual emission bands were found and tunable by the water fraction in THF, and speculatively attributed to the balancing of intramolecular charge transfer (ICT) and locally excited (LE) emission in solution and aggregate states. Furthermore, the potential application in anti‐counterfeiting ink was also explored, indicating the very low concentration (5 ppm) for sufficient distinguishable vision and small colour migration (28 nm) for printing on the filter. The present work provides a new strategy to design organic luminescent structure having widely fluorescent emissions in dual states and a valuable reference for the study of chiral optical materials.

Funder

Natural Science Foundation of Shandong Province

National Natural Science Foundation of China

Publisher

Wiley

Subject

General Chemistry,Catalysis,Organic Chemistry

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