Evidence map›Paper›PMID 35655566›Full record

ArticleChemical science2022

Extended phenothiazines: synthesis, photophysical and redox properties, and efficient photocatalytic oxidative coupling of amines.

Jun Zhou, Lijun Mao, Meng-Xiang Wu, Zhiyong Peng, Yiming Yang, Manfei Zhou, Xiao-Li Zhao, Xueliang Shi, Hai-Bo Yang

Open access · diamondAbstract read
PubMed Full text at PMC Publisher
In one paragraph

Article in Chemical science, 2022. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 5 papers.

0numbers the graph read from it
0cells of the map it votes in
5citing papers in PubMed
2.6field-weighted citation impact, top 9% of its field
1 · What the graph read from it

What it found

Each row is one number read from the abstract, on the scale the paper reported it, with its interval. Left of the dashed line favours the treatment, right favours the comparator. Under each row is the sentence it came from. New to these charts? A ten-minute tutorial.

The abstract states no effect estimate the extractor could read, or names no intervention and outcome on the map, so this paper lights no cell and moves no belief. It is still indexed, cited and linked below.

2 · The registry

The trial behind it

Trials whose registry record cites this paper, or whose number appears in the abstract. A trial that started after this paper was published is citing it as background, not reporting it.

Neither the registry nor the abstract names a trial number. If this is a trial report, that itself is worth knowing.

3 · Its place in the literature

Who cites it

5 citing papers in PubMed, 36 citations in OpenAlex.

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4 · The record

Corrections and comments

PubMed lists nothing against this paper. Absence here is not a guarantee, only a check that was made.

5 · Who and what money

Authors and funding

9 authors at 1 institution in 1 country.

Jun ZhouSchool of Chemistry and Molecular Engineering, Shanghai Key Laboratory of Green Chemistry and Chemical Processes, East China Normal University 3663 N, Zhongshan Road Shanghai 200062 P. R. China xlzhao@chem.ecnu.edu.cn xlshi@chem.ecnu.edu.cn.
Lijun MaoSchool of Chemistry and Molecular Engineering, Shanghai Key Laboratory of Green Chemistry and Chemical Processes, East China Normal University 3663 N, Zhongshan Road Shanghai 200062 P. R. China xlzhao@chem.ecnu.edu.cn xlshi@chem.ecnu.edu.cn.
Meng-Xiang WuSchool of Chemistry and Molecular Engineering, Shanghai Key Laboratory of Green Chemistry and Chemical Processes, East China Normal University 3663 N, Zhongshan Road Shanghai 200062 P. R. China xlzhao@chem.ecnu.edu.cn xlshi@chem.ecnu.edu.cn.
Zhiyong PengSchool of Chemistry and Molecular Engineering, Shanghai Key Laboratory of Green Chemistry and Chemical Processes, East China Normal University 3663 N, Zhongshan Road Shanghai 200062 P. R. China xlzhao@chem.ecnu.edu.cn xlshi@chem.ecnu.edu.cn.
Yiming YangSchool of Chemistry and Molecular Engineering, Shanghai Key Laboratory of Green Chemistry and Chemical Processes, East China Normal University 3663 N, Zhongshan Road Shanghai 200062 P. R. China xlzhao@chem.ecnu.edu.cn xlshi@chem.ecnu.edu.cn.
Manfei ZhouSchool of Chemistry and Molecular Engineering, Shanghai Key Laboratory of Green Chemistry and Chemical Processes, East China Normal University 3663 N, Zhongshan Road Shanghai 200062 P. R. China xlzhao@chem.ecnu.edu.cn xlshi@chem.ecnu.edu.cn.
Xiao-Li ZhaoSchool of Chemistry and Molecular Engineering, Shanghai Key Laboratory of Green Chemistry and Chemical Processes, East China Normal University 3663 N, Zhongshan Road Shanghai 200062 P. R. China xlzhao@chem.ecnu.edu.cn xlshi@chem.ecnu.edu.cn.ORCID https://orcid.org/0000-0002-4458-6432
Xueliang ShiSchool of Chemistry and Molecular Engineering, Shanghai Key Laboratory of Green Chemistry and Chemical Processes, East China Normal University 3663 N, Zhongshan Road Shanghai 200062 P. R. China xlzhao@chem.ecnu.edu.cn xlshi@chem.ecnu.edu.cn.ORCID https://orcid.org/0000-0002-6453-0751
Hai-Bo YangSchool of Chemistry and Molecular Engineering, Shanghai Key Laboratory of Green Chemistry and Chemical Processes, East China Normal University 3663 N, Zhongshan Road Shanghai 200062 P. R. China xlzhao@chem.ecnu.edu.cn xlshi@chem.ecnu.edu.cn.ORCID https://orcid.org/0000-0003-4926-1618
East China Normal University · CN

Funding

No grant is acknowledged in the PubMed record.

6 · The paper itself

Abstract

Herein we successfully developed a ring-fusion approach to extend the conjugation length of phenothiazines and synthesized a series of novel extended phenothiazines 1-5. The intriguing π-conjugation length-dependent photophysical and redox properties of 1-5, and their photocatalytic performance towards visible-light-driven oxidative coupling reactions of amines were systematically investigated. The results indicated that this series of extended phenothiazines exhibited continuous red shifts of light absorption with increasing numbers of fused rings. As compared with the conventional phenothiazine (PTZ), all the extended phenothiazines displayed reversible redox behavior and maintained a strong excited-state reduction potential as well. Consequently, 3, 4 and 5 with longer effective conjugation lengths could efficiently catalyze the oxidative coupling of amines to imines under visible-light irradiation; by comparison, the shorter 1, 2 and PTZ could only catalyze such reactions in the presence of UV light. Moreover, 3 showed superior catalytic performance which can result in better yields within a shorter reaction time, and in a broad substrate scope. Finally, a direct and efficient conversion of amines to imines under sunlight in an air atmosphere was successfully realized. We believe that our study including the new phenothiazine modification methodology and the newly developed extended phenothiazine-based photocatalysts will open up a new way to develop novel phenothiazine-based materials for optoelectronic and catalytic applications.

Identifiers

PMID35655566
PMCPMC9093200
OpenAlexW4226270555

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Registered trials

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Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.