TY - JOUR
T1 - Bright solid-state red-emissive BODIPYs
T2 - facile synthesis and their high-contrast mechanochromic properties
AU - Duan, Chong
AU - Zhou, Yibin
AU - Shan, Guo Gang
AU - Chen, Yuncong
AU - Zhao, Weijun
AU - Yuan, Dandan
AU - Zeng, Lintao
AU - Huang, Xiaobo
AU - Niu, Guangle
N1 - Publisher Copyright:
© The Royal Society of Chemistry.
PY - 2019
Y1 - 2019
N2 - Organic compounds with bright solid-state emission are emerging as versatile materials in many fields. However, traditional fluorescent dyes generally show high-emissive fluorescence in solution but faint or quenched emission in the solid state. Therefore, it remains a great challenge to develop bright solid-state emissive materials based on traditional fluorescent dyes. Herein, we report several solid-state emissive meso-substituted BODIPYs (PhMe3-BODIPY, PhMe-BODIPY, Ph-BODIPY and Me-BODIPY) obtained by using a simple two-step synthesis. Interestingly, these BODIPYs exhibit bright dual-state emission (DSE) with green fluorescence (512-520 nm, fluorescence quantum yield ΦF is up to 85%) in THF and solid-state red emission (601-632 nm, ΦF is up to 32.2%) in the crystalline state. The highly emissive fluorescence in the crystalline state is demonstrated to be due to the formation of J-aggregation. More importantly, the single crystals of the meso-aryl-substituted BODIPYs exhibit an unusual high-contrast mechanochromic property, which displays remarkable fluorescence color changes from red to yellow upon gentle grinding due to the transition from single crystals to microcrystals. Furthermore, strong grinding completely destroys the J-aggregation and leads to the transformation from microcrystals to a free state, hence the fluorescence color becomes green after strong grinding.
AB - Organic compounds with bright solid-state emission are emerging as versatile materials in many fields. However, traditional fluorescent dyes generally show high-emissive fluorescence in solution but faint or quenched emission in the solid state. Therefore, it remains a great challenge to develop bright solid-state emissive materials based on traditional fluorescent dyes. Herein, we report several solid-state emissive meso-substituted BODIPYs (PhMe3-BODIPY, PhMe-BODIPY, Ph-BODIPY and Me-BODIPY) obtained by using a simple two-step synthesis. Interestingly, these BODIPYs exhibit bright dual-state emission (DSE) with green fluorescence (512-520 nm, fluorescence quantum yield ΦF is up to 85%) in THF and solid-state red emission (601-632 nm, ΦF is up to 32.2%) in the crystalline state. The highly emissive fluorescence in the crystalline state is demonstrated to be due to the formation of J-aggregation. More importantly, the single crystals of the meso-aryl-substituted BODIPYs exhibit an unusual high-contrast mechanochromic property, which displays remarkable fluorescence color changes from red to yellow upon gentle grinding due to the transition from single crystals to microcrystals. Furthermore, strong grinding completely destroys the J-aggregation and leads to the transformation from microcrystals to a free state, hence the fluorescence color becomes green after strong grinding.
UR - http://www.scopus.com/inward/record.url?scp=85063288409&partnerID=8YFLogxK
U2 - 10.1039/c8tc06421k
DO - 10.1039/c8tc06421k
M3 - Article
AN - SCOPUS:85063288409
SN - 2050-7526
VL - 7
SP - 3471
EP - 3478
JO - Journal of Materials Chemistry C
JF - Journal of Materials Chemistry C
IS - 12
ER -