Evidence map›Paper›PMID 40645961›Full record

ArticleNature communications2025

Triethylamine vapor-induced cyclization reaction in cocrystals leading to cocrystal-to-polycrystal transformation.

Ling Zhu, Xiaoli Zhao, Yanfei Niu, Lianrui Hu, Weitao Dou, Hai-Bo Yang, Lin Xu, Ben Zhong Tang

Abstract read
PubMed Full text at PMC Publisher
In one paragraph

Article in Nature communications, 2025. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 2 papers.

0numbers the graph read from it
0cells of the map it votes in
2citing papers in PubMed
–field-weighted citation impact
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

2 citing papers in PubMed.

  1. Article
  2. Article
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

8 authors.

Ling ZhuState Key Laboratory of Petroleum Molecular & Process Engineering, Shanghai Key Laboratory of Green Chemistry and Chemical Processes, School of Chemistry and Molecular Engineering, East China Normal University, Shanghai, China.
Xiaoli ZhaoState Key Laboratory of Petroleum Molecular & Process Engineering, Shanghai Key Laboratory of Green Chemistry and Chemical Processes, School of Chemistry and Molecular Engineering, East China Normal University, Shanghai, China.
Yanfei NiuState Key Laboratory of Petroleum Molecular & Process Engineering, Shanghai Key Laboratory of Green Chemistry and Chemical Processes, School of Chemistry and Molecular Engineering, East China Normal University, Shanghai, China.
Lianrui HuState Key Laboratory of Petroleum Molecular & Process Engineering, Shanghai Key Laboratory of Green Chemistry and Chemical Processes, School of Chemistry and Molecular Engineering, East China Normal University, Shanghai, China. lrhu@chem.ecnu.edu.cn.ORCID http://orcid.org/0000-0002-4044-5640
Weitao DouState Key Laboratory of Petroleum Molecular & Process Engineering, Shanghai Key Laboratory of Green Chemistry and Chemical Processes, School of Chemistry and Molecular Engineering, East China Normal University, Shanghai, China.ORCID http://orcid.org/0000-0003-1497-0414
Hai-Bo YangState Key Laboratory of Petroleum Molecular & Process Engineering, Shanghai Key Laboratory of Green Chemistry and Chemical Processes, School of Chemistry and Molecular Engineering, East China Normal University, Shanghai, China.ORCID http://orcid.org/0000-0003-4926-1618
Lin XuState Key Laboratory of Petroleum Molecular & Process Engineering, Shanghai Key Laboratory of Green Chemistry and Chemical Processes, School of Chemistry and Molecular Engineering, East China Normal University, Shanghai, China. lxu@chem.ecnu.edu.cn.ORCID http://orcid.org/0000-0002-6332-1376
Ben Zhong TangSchool of Science and Engineering, Shenzhen Institute of Molecular Aggregate Science and Technology, The Chinese University of Hong Kong, Shenzhen (CUHK-Shenzhen), Shenzhen, Guangdong, China. tangbenz@cuhk.edu.cn.ORCID http://orcid.org/0000-0002-0293-964X

Funding

National Natural Science Foundation of China (National Science Foundation of China) 22371076Science and Technology Commission of Shanghai Municipality (Shanghai Municipal Science and Technology Commission) 22JC1403900 and 21520710200
6 · The paper itself

Abstract

The structural transformation of crystals triggered by external stimuli is a fascinating area in materials science and supramolecular chemistry. Despite the potential of organic reactions driving crystal conversions, its exploration remains limited, primarily due to challenges in maintaining crystallinity during significant structural changes. In this study, we present an intriguing example of a triethylamine vapor-induced cyclization reaction in a cocrystal, leading to its conversion into polycrystals. Initially, a charge transfer cocrystal with hydrogen-bond interactions denoted as AOTC, was prepared from 9-anthracene-substituted indolino-oxazolidine (Box) in its open form and 1,2,4,5-tetracyanobenzene (TCNB). Treatment of cocrystal AOTC with triethylamine vapor effectively induced a cyclization reaction, resulting in the formation of single-crystal AIC (closed form Box) and cocrystal ACTC (a cocrystal of AIC and TCNB), both of which were suitable for direct X-ray single crystal diffraction analysis. Experimental and theoretical analysis revealed that the cocrystal-to-polycrystal transformation was primarily driven by the cyclization reaction and the synergistic effects of intermolecular D-A and C-H···N hydrogen bond interactions. Additionally, this unique base-induced transformation was utilized for information storage applications. This research not only provides a rare instance of cocrystal-to-polycrystal transformation through a simple yet effective approach but also offers a strategy for crystal engineering.

Identifiers

PMID40645961
PMCPMC12254319

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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.