Regulating Crystal Packing by Terminal tert-Butylation for Enhanced Solid-State Emission and Efficacious Charge Transport in an Anthracene-Based Molecular Crystal

Jie Li; Zhengsheng Qin; Yajing Sun; Yonggang Zhen; Jie Liu; Ye Zou; Chunlei Li; Xueying Lu; Lang Jiang; Xiaotao Zhang; Deyang Ji; Liqiang Li; Huanli Dong; Wenping Hu

doi:10.1002/anie.202206825

Regulating Crystal Packing by Terminal tert-Butylation for Enhanced Solid-State Emission and Efficacious Charge Transport in an Anthracene-Based Molecular Crystal

Angew Chem Int Ed Engl. 2022 Nov 7;61(45):e202206825. doi: 10.1002/anie.202206825. Epub 2022 Sep 6.

Authors

Jie Li¹, Zhengsheng Qin², Yajing Sun³, Yonggang Zhen², Jie Liu², Ye Zou², Chunlei Li², Xueying Lu³, Lang Jiang², Xiaotao Zhang¹, Deyang Ji¹, Liqiang Li^{1

4}, Huanli Dong², Wenping Hu^{3

4

5}

Affiliations

¹ Tianjin Key Laboratory of Molecular Optoelectronic Sciences, Department of Chemistry, Institute of Molecular Aggregation Science, Tianjin University, Tianjin, 300072, China.
² Beijing National Laboratory for Molecular Sciences, Key laboratory of Organic Solids, Institute of Chemistry, Chinese Academy of Sciences, Beijing, 100190, China.
³ Tianjin Key Laboratory of Molecular Optoelectronic Sciences, Department of Chemistry, School of Science, Tianjin University, Tianjin, 300072, China.
⁴ Joint School of National University of Singapore and Tianjin University, International Campus of Tianjin University, Binhai New City, Fuzhou, 350207, China.
⁵ Haihe Laboratory of Sustainable Chemical Transformations, Tianjin, 300192, China.

PMID: 35989244
DOI: 10.1002/anie.202206825

Abstract

Organic semiconductors with combinative high carrier mobility and efficient solid-state emission are full of challenges but urgently pursued for developing new emerging optoelectronics. Herein, by delicately regulating the crystal packing of an anthracene-based molecular crystal via terminal tert-butylation, we developed a superior high mobility emissive molecule, 2,6-di(6-tert-butylnaphthyl)anthracene (TBU-DNA). The unique "slipped herringbone" packing motif of TBU-DNA enables its appropriate exciton-exciton coupling and electron-phonon coupling, thus resulting in remarkably high solid-state emission (photoluminescence quantum yield, Φ_F ≈74.9 %) and efficacious charge transport (carrier mobility, μ=5.0 cm² V^-1 s^-1 ). Furthermore, OLETs based on TBU-DNA show an external quantum efficiency (EQE) of 1.8 %, which is among the highest EQE values for single component OLETs reported till now. This work presents a crystal engineering strategy via exquisite molecular design to realize high mobility emissive organic semiconductors.

Keywords: Charge Transport; Crystal Engineering; Light Emission; Molecular Crystals; Organic Semiconductor.

Abstract

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