Bottom-Up Preparation of Twisted Graphene Nanoribbons by Cu-Catalyzed Deoxygenative Coupling
Dr. Yuan Gao
State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Tianshui Southern Road 222, Lanzhou, 730000 Gansu, Province, China
Contribution: Data curation (lead), Formal analysis (lead), Investigation (lead), Writing - review & editing (supporting)
Search for more papers by this authorDr. Xinqiang Hua
State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Tianshui Southern Road 222, Lanzhou, 730000 Gansu, Province, China
Contribution: Investigation (supporting), Software (lead)
Search for more papers by this authorDr. Wei Jiang
State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Tianshui Southern Road 222, Lanzhou, 730000 Gansu, Province, China
Contribution: Investigation (supporting), Methodology (supporting)
Search for more papers by this authorProf. Dr. Chun-Lin Sun
State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Tianshui Southern Road 222, Lanzhou, 730000 Gansu, Province, China
Contribution: Data curation (supporting), Formal analysis (supporting)
Search for more papers by this authorProf. Dr. Chengshan Yuan
State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Tianshui Southern Road 222, Lanzhou, 730000 Gansu, Province, China
Contribution: Data curation (supporting), Formal analysis (supporting), Investigation (supporting)
Search for more papers by this authorProf. Dr. Zitong Liu
State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Tianshui Southern Road 222, Lanzhou, 730000 Gansu, Province, China
Contribution: Conceptualization (supporting), Data curation (supporting), Formal analysis (supporting)
Search for more papers by this authorProf. Dr. Hao-Li Zhang
State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Tianshui Southern Road 222, Lanzhou, 730000 Gansu, Province, China
Contribution: Conceptualization (supporting), Funding acquisition (supporting), Investigation (supporting)
Search for more papers by this authorCorresponding Author
Prof. Dr. Xiangfeng Shao
State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Tianshui Southern Road 222, Lanzhou, 730000 Gansu, Province, China
Contribution: Conceptualization (lead), Formal analysis (equal), Funding acquisition (lead), Investigation (equal), Project administration (lead), Supervision (lead), Writing - original draft (lead), Writing - review & editing (lead)
Search for more papers by this authorDr. Yuan Gao
State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Tianshui Southern Road 222, Lanzhou, 730000 Gansu, Province, China
Contribution: Data curation (lead), Formal analysis (lead), Investigation (lead), Writing - review & editing (supporting)
Search for more papers by this authorDr. Xinqiang Hua
State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Tianshui Southern Road 222, Lanzhou, 730000 Gansu, Province, China
Contribution: Investigation (supporting), Software (lead)
Search for more papers by this authorDr. Wei Jiang
State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Tianshui Southern Road 222, Lanzhou, 730000 Gansu, Province, China
Contribution: Investigation (supporting), Methodology (supporting)
Search for more papers by this authorProf. Dr. Chun-Lin Sun
State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Tianshui Southern Road 222, Lanzhou, 730000 Gansu, Province, China
Contribution: Data curation (supporting), Formal analysis (supporting)
Search for more papers by this authorProf. Dr. Chengshan Yuan
State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Tianshui Southern Road 222, Lanzhou, 730000 Gansu, Province, China
Contribution: Data curation (supporting), Formal analysis (supporting), Investigation (supporting)
Search for more papers by this authorProf. Dr. Zitong Liu
State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Tianshui Southern Road 222, Lanzhou, 730000 Gansu, Province, China
Contribution: Conceptualization (supporting), Data curation (supporting), Formal analysis (supporting)
Search for more papers by this authorProf. Dr. Hao-Li Zhang
State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Tianshui Southern Road 222, Lanzhou, 730000 Gansu, Province, China
Contribution: Conceptualization (supporting), Funding acquisition (supporting), Investigation (supporting)
Search for more papers by this authorCorresponding Author
Prof. Dr. Xiangfeng Shao
State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Tianshui Southern Road 222, Lanzhou, 730000 Gansu, Province, China
Contribution: Conceptualization (lead), Formal analysis (equal), Funding acquisition (lead), Investigation (equal), Project administration (lead), Supervision (lead), Writing - original draft (lead), Writing - review & editing (lead)
Search for more papers by this authorGraphical Abstract
A series of highly twisted and fully armchair-edged graphene nanoribbons (AGNRs) have been synthesized by Cu-catalyzed deoxygenative coupling. These twisted AGNRs have lengths up to 2.65 nm and display strong emission with a fluorescence quantum yield up to 81 %.
Abstract
Graphene nanoribbons (GNRs) are promising in organic optoelectronic materials, and their properties largely depend on the size, edge, and conformation. Herein, the fully armchair-edged GNRs (AGNRs) with lengths up to 2.65 nm by using a Cu-catalyzed deoxygenative coupling as a key step. The resulting AGNRs (2HBT, 3HBT, and 4HBT) possess highly twisted π-scaffolds, and the torsion angles between the adjacent triphenylene moieties are larger than 32°, as proved by crystallographic analyses. Theoretical and spectroscopic studies show that the butoxy groups endow AGNRs with electron-rich features, the extension of the π-system from 2HBT to 4HBT reinforces S0→S1 excitation, and the distortion of the π-scaffold enhances the fluorescence quantum yield (ΦF). In particular, 4HBT has the lowest oxidation potential (Eox1=0.55 V vs. SCE) and displays red fluorescence with a ΦF value of 81 %.
Conflict of interest
The authors declare no conflict of interest.
Open Research
Data Availability Statement
The data that support the findings of this study are available in the supplementary material of this article.
Supporting Information
As a service to our authors and readers, this journal provides supporting information supplied by the authors. Such materials are peer reviewed and may be re-organized for online delivery, but are not copy-edited or typeset. Technical support issues arising from supporting information (other than missing files) should be addressed to the authors.
| Filename | Description |
|---|---|
| anie202210924-sup-0001-2HBT.cif1.2 MB | Supporting Information |
| anie202210924-sup-0001-3HBT.cif2.3 MB | Supporting Information |
| anie202210924-sup-0001-4HBT.cif5.1 MB | Supporting Information |
| anie202210924-sup-0001-Compound_2.cif1.6 MB | Supporting Information |
| anie202210924-sup-0001-Compound_3.cif4.2 MB | Supporting Information |
| anie202210924-sup-0001-Compound_6.cif1.5 MB | Supporting Information |
| anie202210924-sup-0001-misc_information.pdf11.6 MB | Supporting Information |
Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article.
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