Multi-Functional 2D Covalent Organic Frameworks with Diketopyrrolopyrrole as Electron Acceptor

Liang Luo; Chunbin Li; Yuancheng Wang; Pinyu Chen; Zhaoqiong Zhou; Tianwen Chen; Kunlan Wu; San-Yuan Ding; Luxi Tan; Jianguo Wang; Xiangfeng Shao; Zitong Liu

doi:10.1002/smll.202402993

Multi-Functional 2D Covalent Organic Frameworks with Diketopyrrolopyrrole as Electron Acceptor

Small. 2024 May 15:e2402993. doi: 10.1002/smll.202402993. Online ahead of print.

Authors

Affiliations

¹ State Key Laboratory of Applied Organic Chemistry (SKLAOC), Key Laboratory of Special Function Materials and Structure Design, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou, 730000, China.
² College of Chemistry and Chemical Engineering, Inner Mongolia Key Laboratory of Fine Organic Synthesis, Inner Mongolia University, Hohhot, 010021, China.
³ College of Polymer Science and Engineering, Qingdao University of Science and Technology, Qingdao, 266042, China.
⁴ School of Chemistry and Chemical Engineering, Chongqing University, Chongqing, 400044, P. R. China.

PMID: 38750614
DOI: 10.1002/smll.202402993

Abstract

2D covalent organic framework (COF) materials with extended conjugated structure and periodic columnar π-arrays exhibit promising applications in organic optoelectronics. However, there is a scarcity of reports on optoelectronic COFs, mainly due to the lack of suitable π-skeletons. Here, two multi-functional optoelectronic 2D COFs DPP-TPP-COF and DPP-TBB-COF are constructed with diketopyrrolopyrrole as electron acceptor (A), and 1,3,6,8-tetraphenylpyrene and 1,3,5-triphenylbenzene as electron donor (D) through imine bonds. Both 2D COFs showed good crystallinities and AA stacking with a rhombic framework for DPP-TPP-COF and hexagonal one for DPP-TBB-COF, respectively. The electron D-A and ordered intermolecular packing structures endow the COFs with broad UV-vis absorptions and narrow bandgaps along with suitable HOMO/LUMO energy levels, resulting in multi-functional optoelectronic properties, including photothermal conversion, supercapacitor property, and ambipolar semiconducting behavior. Among them, DPP-TPP-COF exhibits a high photothermal conversion efficiency of 47% under 660 nm laser irradiation, while DPP-TBB-COF exhibits superior specific capacitance of 384 F g^-1. Moreover, P-type doping and N-type doping are achieved by iodine and tetrakis(dimethylamino)ethylene on a single host COF, resulting in ambipolar semiconducting behavior. These results provide a paradigm for the application of multi-functional optoelectronic COF materials.

Keywords: ambipolar semiconducting property; covalent organic framework; diketopyrrolopyrrole; optoelectronic property; photothermal conversion.

Abstract

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