Tuning Photoexcited Charge Transfer in Imine-Linked Two-Dimensional Covalent Organic Frameworks

Feng, Tiantian; Streater, Daniel; Sun, Bing; Duisenova, Korlan; Wang, Dong; Liu, Yi; Huang, Jier; Zhang, Jian

doi:10.1021/acs.jpclett.1c04163

Title: Tuning Photoexcited Charge Transfer in Imine-Linked Two-Dimensional Covalent Organic Frameworks

Journal Article · 03 February 2022 · Journal of Physical Chemistry Letters

DOI: https://doi.org/10.1021/acs.jpclett.1c04163 · OSTI ID:1865056

Feng, Tiantian ^[1]; Streater, Daniel ^[2];

^[3]; Duisenova, Korlan ^[2];

^[4];

^[5];

^[2];

^[5]

China Univ. of Geosciences, Beijing (China); Chinese Academy of Sciences (CAS), Beijing (China); Marquette University
Marquette Univ., Milwaukee, WI (United States)
China Univ. of Geosciences, Beijing (China)
Chinese Academy of Sciences (CAS), Beijing (China)
Lawrence Berkeley National Lab. (LBNL), Berkeley, CA (United States)

The generation of a long-lived charge-separated state in versatile π-conjugated two-dimensional covalent organic frameworks (2D COFs), a process essential to extending their great potentials in advanced semiconducting applications, is yet fully elucidated. Herein, we report a systematic investigation of the photophysical properties of three highly crystalline imine-linked 2D COFs using steady-state and transient absorption spectroscopy accompanied by time-dependent density functional theory (TDDFT) calculations. The different electron affinity between 5,5',5''-(1,3,5-benzenetriyl)-tris(2-pyridinecarboxaldehyde) (BTPA) and three tunable electron-donating/accepting triamine monomers dominated the formation of the excited state, charge transfer direction and lifetime. A prominent charge transfer from electron-rich 4,4',4''-triaminotriphenylamine (TAPA) to BTPA in COFTAPA-BTPA led to the long-lived charge-separated state, which was attributed to a greater degree of delocalization compared to the two other COFs. Furthermore, these results provide fundamental insight into the importance of structure-property correlation for designing advanced photoactive 2D COF materials with the efficient charge transfer and long-lived charge-separated state.

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Research Organization:: Marquette Univ., Milwaukee, WI (United States); Marquette University, Milwaukee, WI (United States)

Sponsoring Organization:: USDOE Office of Science (SC), Basic Energy Sciences (BES)

Grant/Contract Number:: AC02-05CH11231; SC0020122

OSTI ID:: 1865056

Journal Information:: Journal of Physical Chemistry Letters, Journal Name: Journal of Physical Chemistry Letters Journal Issue: 6 Vol. 13; ISSN 1948-7185

Publisher:: American Chemical SocietyCopyright Statement

Country of Publication:: United States

Language:: English

References (33)

Covalent Organic Frameworks: Structures, Synthesis, and Applications Lohse, Maria S.; Bein, Thomas Advanced Functional Materials, Vol. 28, Issue 33 https://doi.org/10.1002/adfm.201705553	journal	July 2018
Ultrahigh Responsivity Photodetectors of 2D Covalent Organic Frameworks Integrated on Graphene Xiong, Yifeng; Liao, Qiaobo; Huang, Zhengping Advanced Materials, Vol. 32, Issue 9 https://doi.org/10.1002/adma.201907242	journal	January 2020
Antifouling Field‐Effect Transistor Sensing Interface Based on Covalent Organic Frameworks Yang, Lei; Jin, Yuqing; Wang, Xuejun Advanced Electronic Materials, Vol. 6, Issue 5 https://doi.org/10.1002/aelm.201901169	journal	March 2020
Photoactive and Conducting Covalent Organic Frameworks Medina, Dana D.; Sick, Torben; Bein, Thomas Advanced Energy Materials, Vol. 7, Issue 16 https://doi.org/10.1002/aenm.201700387	journal	June 2017
High-Rate Charge-Carrier Transport in Porphyrin Covalent Organic Frameworks: Switching from Hole to Electron to Ambipolar Conduction Feng, Xiao; Liu, Lili; Honsho, Yoshihito Angewandte Chemie International Edition, Vol. 51, Issue 11 https://doi.org/10.1002/anie.201106203	journal	January 2012
Charge Dynamics in A Donor-Acceptor Covalent Organic Framework with Periodically Ordered Bicontinuous Heterojunctions Jin, Shangbin; Ding, Xuesong; Feng, Xiao Angewandte Chemie International Edition, Vol. 52, Issue 7 https://doi.org/10.1002/anie.201209513	journal	January 2013
Decoding the Morphological Diversity in Two Dimensional Crystalline Porous Polymers by Core Planarity Modulation Halder, Arjun; Kandambeth, Sharath; Biswal, Bishnu P. Angewandte Chemie International Edition, Vol. 55, Issue 27 https://doi.org/10.1002/anie.201600087	journal	March 2016
Vinylene‐Linked Covalent Organic Frameworks by Base‐Catalyzed Aldol Condensation Acharjya, Amitava; Pachfule, Pradip; Roeser, Jérôme Angewandte Chemie International Edition, Vol. 58, Issue 42 https://doi.org/10.1002/anie.201905886	journal	September 2019
Recent Advances on Conductive 2D Covalent Organic Frameworks Bian, Gang; Yin, Jun; Zhu, Jian Small, Vol. 17, Issue 22 https://doi.org/10.1002/smll.202006043	journal	February 2021
Two-dimensional porphyrin- and phthalocyanine-based covalent organic frameworks Wang, Hongmin; Ding, Huimin; Meng, Xiangshi Chinese Chemical Letters, Vol. 27, Issue 8 https://doi.org/10.1016/j.cclet.2016.05.020	journal	August 2016
Dynamic Covalent Synthesis of Crystalline Porous Graphitic Frameworks Li, Xinle; Wang, Hongxia; Chen, Hao Chem, Vol. 6, Issue 4 https://doi.org/10.1016/j.chempr.2020.01.011	journal	April 2020
Chemistry of Covalent Organic Frameworks Waller, Peter J.; Gándara, Felipe; Yaghi, Omar M. Accounts of Chemical Research, Vol. 48, Issue 12 https://doi.org/10.1021/acs.accounts.5b00369	journal	November 2015
Oriented Covalent Organic Framework Film on Graphene for Robust Ambipolar Vertical Organic Field-Effect Transistor Sun, Bing; Zhu, Chen-Hui; Liu, Yi Chemistry of Materials, Vol. 29, Issue 10 https://doi.org/10.1021/acs.chemmater.7b00800	journal	May 2017
H ₂ Evolution with Covalent Organic Framework Photocatalysts Banerjee, Tanmay; Gottschling, Kerstin; Savasci, Gökcen ACS Energy Letters, Vol. 3, Issue 2 https://doi.org/10.1021/acsenergylett.7b01123	journal	January 2018
Identification of Prime Factors to Maximize the Photocatalytic Hydrogen Evolution of Covalent Organic Frameworks Ghosh, Samrat; Nakada, Akinobu; Springer, Maximilian A. Journal of the American Chemical Society https://doi.org/10.1021/jacs.0c02633	journal	May 2020
Large Exciton Diffusion Coefficients in Two-Dimensional Covalent Organic Frameworks with Different Domain Sizes Revealed by Ultrafast Exciton Dynamics Flanders, Nathan C.; Kirschner, Matthew S.; Kim, Pyosang Journal of the American Chemical Society, Vol. 142, Issue 35 https://doi.org/10.1021/jacs.0c05404	journal	July 2020
Creation of Superheterojunction Polymers via Direct Polycondensation: Segregated and Bicontinuous Donor–Acceptor π-Columnar Arrays in Covalent Organic Frameworks for Long-Lived Charge Separation Jin, Shangbin; Supur, Mustafa; Addicoat, Matthew Journal of the American Chemical Society, Vol. 137, Issue 24 https://doi.org/10.1021/jacs.5b03553	journal	June 2015
Spectrally Switchable Photodetection with Near-Infrared-Absorbing Covalent Organic Frameworks Bessinger, Derya; Ascherl, Laura; Auras, Florian Journal of the American Chemical Society, Vol. 139, Issue 34 https://doi.org/10.1021/jacs.7b06599	journal	August 2017
Conversion of Imine to Oxazole and Thiazole Linkages in Covalent Organic Frameworks Waller, Peter J.; AlFaraj, Yasmeen S.; Diercks, Christian S. Journal of the American Chemical Society, Vol. 140, Issue 29 https://doi.org/10.1021/jacs.8b05830	journal	June 2018
Covalent Organic Frameworks: Chemistry beyond the Structure Kandambeth, Sharath; Dey, Kaushik; Banerjee, Rahul Journal of the American Chemical Society, Vol. 141, Issue 5 https://doi.org/10.1021/jacs.8b10334	journal	November 2018
Two-Dimensional Chemiresistive Covalent Organic Framework with High Intrinsic Conductivity Meng, Zheng; Stolz, Robert M.; Mirica, Katherine A. Journal of the American Chemical Society, Vol. 141, Issue 30 https://doi.org/10.1021/jacs.9b03441	journal	June 2019
Excited-State Dynamics in Fully Conjugated 2D Covalent Organic Frameworks Jakowetz, Andreas C.; Hinrichsen, Ture F.; Ascherl, Laura Journal of the American Chemical Society, Vol. 141, Issue 29 https://doi.org/10.1021/jacs.9b03956	journal	June 2019
Delocalization and Mobility of Charge Carriers in Covalent Organic Frameworks Patwardhan, Sameer; Kocherzhenko, Aleksey A.; Grozema, Ferdinand C. The Journal of Physical Chemistry C, Vol. 115, Issue 23 https://doi.org/10.1021/jp202399u	journal	May 2011
Covalent organic frameworks: a materials platform for structural and functional designs Huang, Ning; Wang, Ping; Jiang, Donglin Nature Reviews Materials, Vol. 1, Issue 10 https://doi.org/10.1038/natrevmats.2016.68	journal	September 2016
Conjugated organic framework with three-dimensionally ordered stable structure and delocalized π clouds Guo, Jia; Xu, Yanhong; Jin, Shangbin Nature Communications, Vol. 4, Issue 1 https://doi.org/10.1038/ncomms3736	journal	November 2013
Solvatochromic covalent organic frameworks Ascherl, Laura; Evans, Emrys W.; Hennemann, Matthias Nature Communications, Vol. 9, Issue 1 https://doi.org/10.1038/s41467-018-06161-w	journal	September 2018
Ultrafast charge transfer coupled with lattice phonons in two-dimensional covalent organic frameworks Kim, Tae Wu; Jun, Sunhong; Ha, Yoonhoo Nature Communications, Vol. 10, Issue 1 https://doi.org/10.1038/s41467-019-09872-w	journal	April 2019
Chemically stable polyarylether-based covalent organic frameworks Guan, Xinyu; Li, Hui; Ma, Yunchao Nature Chemistry, Vol. 11, Issue 6 https://doi.org/10.1038/s41557-019-0238-5	journal	April 2019
Covalent organic frameworks (COFs): from design to applications Ding, San-Yuan; Wang, Wei Chem. Soc. Rev., Vol. 42, Issue 2 https://doi.org/10.1039/C2CS35072F	journal	January 2013
Optoelectronic processes in covalent organic frameworks Keller, Niklas; Bein, Thomas Chemical Society Reviews, Vol. 50, Issue 3 https://doi.org/10.1039/D0CS00793E	journal	January 2021
The atom, the molecule, and the covalent organic framework Diercks, Christian S.; Yaghi, Omar M. Science, Vol. 355, Issue 6328 https://doi.org/10.1126/science.aal1585	journal	March 2017
Seeded growth of single-crystal two-dimensional covalent organic frameworks Evans, Austin M.; Parent, Lucas R.; Flanders, Nathan C. Science, Vol. 361, Issue 6397 https://doi.org/10.1126/science.aar7883	journal	June 2018
Glotaran : A Java -Based Graphical User Interface for the R Package TIMP Snellenburg, Joris J.; Laptenok, Sergey P.; Seger, Ralf Journal of Statistical Software, Vol. 49, Issue 3 https://doi.org/10.18637/jss.v049.i03	journal	January 2012

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Title: Tuning Photoexcited Charge Transfer in Imine-Linked Two-Dimensional Covalent Organic Frameworks

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