Pyridyl substitution at the 2,6-positions of anthracene toward crystal polymorphs with distinct optical characteristics

Geetha Bolla; Junfeng Guo; Huijuan Zhao; Shaokai Lv; Jie Liu; Yang Li; Yonggang Zhen; Qing Liao; Xinran Wang; Hongbing Fu; Huanli Dong; Zongrui Wang; Zhaohui Wang; Wenping Hu

doi:10.1039/D2CE00899H

Pyridyl substitution at the 2,6-positions of anthracene toward crystal polymorphs with distinct optical characteristics†

Geetha Bolla,

‡^a Junfeng Guo,‡^abc Huijuan Zhao,‡^d Shaokai Lv,^e Jie Liu,^a Yang Li,^f Yonggang Zhen,

*^bg Qing Liao,

^e Xinran Wang,^h Hongbing Fu,

^e Huanli Dong,

^a Zongrui Wang,

^b Zhaohui Wang

ⁱ and Wenping Hu*^j

Author affiliations

* Corresponding authors

^a National Laboratory for Molecular Sciences, Key Laboratory of Organic Solids, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, China

^b Beijing Advanced Innovation Center for Soft Matter Science and Engineering & State Key Laboratory of Organic–Inorganic Composites, Beijing University of Chemical Technology, Beijing 100029, China
E-mail: zhenyg@buct.edu.cn

^c University of the Chinese Academy of Sciences, Beijing 100039, China

^d State Key Laboratory for Organic Electronics and Information Displays (KLOEID), Institute of Advanced Materials (IAM), School of Materials Science and Engineering, Nanjing University of Posts and Telecommunications, Nanjing 210023, China

^e Beijing Key Laboratory for Optical Materials and Photonic Devices, Department of Chemistry, Capital Normal University, Beijing 100048, China

^f Normal College, Shenyang University, Shenyang 110044, China

^g State Key Laboratory of Optoelectronic Materials and Technologies, Sun Yat-sen University, Guangdong 510275, China

^h National Laboratory of Solid State Microstructures, School of Electronic Science and Engineering, Collaborative Innovation Center of Advanced Microstructures, Nanjing University, Nanjing 210093, China

ⁱ Key Laboratory of Organic Optoelectronics and Molecular Engineering, Department of Chemistry, Tsinghua University, Beijing 100084, China

^j Tianjin Key Laboratory of Molecular Optoelectronic Science, Department of Chemistry, School of Science, Tianjin University, Tianjin 300072, China
E-mail: huwp@tju.edu.cn

Abstract

For molecular materials, the packing motif plays a pivotal role in determining the optoelectronic characteristics, and it can be tailored via altering not only the molecular structure but also the crystal polymorph. However, it remains a long-standing difficulty for one molecular material to achieve both herringbone packing and 1D slipped stacking, shielding the relationship between the two classic motifs and the functional properties. Herein, we demonstrate that pyridyl substitution at the 2,6-positions of anthracene opens up the possibility of crystal polymorphism from herringbone packing to 1D slipped stacking. The two crystal polymorphs show distinct crystal morphologies, emission spectra, optical anisotropy, and waveguiding properties, shedding light on the relationship between the packing arrangement and optical characteristics based on the same molecular structure.

CrystEngComm

Pyridyl substitution at the 2,6-positions of anthracene toward crystal polymorphs with distinct optical characteristics†

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Pyridyl substitution at the 2,6-positions of anthracene toward crystal polymorphs with distinct optical characteristics

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