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Towards the Tetrabenzo-Fused Circumazulene via In-Solution and On-Surface Synthesis 通过溶液内和表面合成制备四苯并融合环马祖琳
Organic Materials Pub Date : 2024-06-14 DOI: 10.1055/a-2333-9789
Fupeng Wu, Wangwei Xu, Yubin Fu, Renxiang Liu, Lin Yang, Pascal Ruffieux, Roman Fasel, Ji Ma, Xinliang Feng
{"title":"Towards the Tetrabenzo-Fused Circumazulene via In-Solution and On-Surface Synthesis","authors":"Fupeng Wu, Wangwei Xu, Yubin Fu, Renxiang Liu, Lin Yang, Pascal Ruffieux, Roman Fasel, Ji Ma, Xinliang Feng","doi":"10.1055/a-2333-9789","DOIUrl":"https://doi.org/10.1055/a-2333-9789","url":null,"abstract":"<p>The synthesis of circumazulene, a nonalternant isomer of circumnaphthalene, and its π-expanded derivatives poses a considerable challenge due to the lack of a suitable synthetic strategy. In this work, we present our efforts toward achieving tetrabenzo-fused circumazulene (<b>1</b>) through both solution and on-surface syntheses. In the case of in-solution synthesis, we obtained a product (<b>P</b>) with the desired target mass, but the structural verification proved to be challenging owing to the presence of various structural isomers. In the on-surface synthesis approach, a series of unexpected azulene-embedded nanographenes were obtained, including a molecule with an additional pentagonal ring (<b>U1</b>) based on the backbone of <b>1</b>. Furthermore, theoretical calculations were conducted to shed light on these unexpected structures and to investigate their aromaticity. This work opens a new avenue for the design and synthesis of novel nonalternant graphene nanostructures incorporating circumarene.</p> ","PeriodicalId":93348,"journal":{"name":"Organic Materials","volume":"32 1","pages":""},"PeriodicalIF":0.0,"publicationDate":"2024-06-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141548083","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
2D Conductive Metal–Organic Frameworks for Electrochemical Energy Application 用于电化学能源应用的二维导电金属有机框架
Organic Materials Pub Date : 2024-05-17 DOI: 10.1055/s-0044-1786500
Ruofan Li, Xiaoli Yan, Long Chen
{"title":"2D Conductive Metal–Organic Frameworks for Electrochemical Energy Application","authors":"Ruofan Li, Xiaoli Yan, Long Chen","doi":"10.1055/s-0044-1786500","DOIUrl":"https://doi.org/10.1055/s-0044-1786500","url":null,"abstract":"<p>Two-dimensional conductive metal–organic frameworks (2D <i>c</i>-MOFs) have attracted research attention, benefitting from their unique properties such as superior electronic conductivity, designable topologies, and well-defined catalytic/redox-active sites. These advantages enable 2D <i>c</i>-MOFs as promising candidates in electrochemical energy applications, including supercapacitors, batteries and electrocatalysts. This mini-review mainly highlights recent advancements of 2D <i>c</i>-MOFs in the utilization for electrochemical energy storage, as well as the forward-looking perspective on the future prospects of 2D <i>c</i>-MOFs in the field of electrochemical energy.</p> <p>Table of content:</p> <p>1 Introduction</p> <p>2 Design Principles of 2D <i>c</i>-MOFs</p> <p>3 Synthesis of 2D <i>c</i>-MOFs</p> <p>4 2D <i>c</i>-MOFs for Electrochemical Energy Storage</p> <p>4.1 Supercapacitors</p> <p>4.2 Metallic Batteries</p> <p>4.2.1 Lithium-Ion Batteries</p> <p>4.2.2 Sodium-Ion Batteries</p> <p>4.2.3 Zinc-Ion Batteries</p> <p>4.2.4 Sodium–Iodine Batteries</p> <p>4.2.5 Lithium–Sulfur Batteries</p> <p>4.2.6 Potassium-Ion Batteries</p> <p>5 2D <i>c</i>-MOFs for Electrochemical Energy Conversion</p> <p>6 Conclusions and Outlook</p> ","PeriodicalId":93348,"journal":{"name":"Organic Materials","volume":"40 1","pages":""},"PeriodicalIF":0.0,"publicationDate":"2024-05-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141058996","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Metal-Catalyzed Multi-Component Approach to Quinoline-Linked Covalent Organic Frameworks 金属催化多组分喹啉连接共价有机框架方法
Organic Materials Pub Date : 2024-05-17 DOI: 10.1055/s-0044-1787016
Xianghao Han, Shuda Dong, Xiao Feng
{"title":"Metal-Catalyzed Multi-Component Approach to Quinoline-Linked Covalent Organic Frameworks","authors":"Xianghao Han, Shuda Dong, Xiao Feng","doi":"10.1055/s-0044-1787016","DOIUrl":"https://doi.org/10.1055/s-0044-1787016","url":null,"abstract":"<p>The development of new reaction chemistry is highly desirable to construct new structural and functional covalent organic frameworks (COFs). Benefiting from the extremely large database of metal-catalyzed reaction database, we herein develop a new synthetic strategy that can generate quinoline-linked COFs via a silver-catalyzed three-component one-pot reaction and achieve functionalization by the simple replacement of alcohols. This metal-catalyzed approach to the construction of robust COF structures characterized by extended π-conjugation holds the potential to pave a novel pathway in the synthesis of COF materials endowed with both heightened stability and functionality.</p> ","PeriodicalId":93348,"journal":{"name":"Organic Materials","volume":"92 1","pages":""},"PeriodicalIF":0.0,"publicationDate":"2024-05-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141058938","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
A Nonbenzenoid 3D Nanographene Containing 5/6/7/8-Membered Rings 一种含有 5/6/7/8 个分子环的非苯并三维纳米石墨烯
Organic Materials Pub Date : 2024-04-30 DOI: 10.1055/a-2291-8774
Pengcai Liu, Hao-Han Lv, Rui Xue, Xiao-Yu Tang, Xing-Yu Chen, Liping Qi, Xiao-Ye Wang
{"title":"A Nonbenzenoid 3D Nanographene Containing 5/6/7/8-Membered Rings","authors":"Pengcai Liu, Hao-Han Lv, Rui Xue, Xiao-Yu Tang, Xing-Yu Chen, Liping Qi, Xiao-Ye Wang","doi":"10.1055/a-2291-8774","DOIUrl":"https://doi.org/10.1055/a-2291-8774","url":null,"abstract":"<p>Nanographenes (NGs) have attracted continuous attention in recent years owing to their opened bandgaps and optoelectronic applications. Especially, nonbenzenoid NGs containing non-six-membered rings have been developed rapidly due to their unique structures and properties. In this work, we employ nonbenzenoid acepleiadylene (APD) and the cyclooctatetraene (COT) moiety to construct the first three-dimensional (3D) NG containing 5/6/7/8-membered rings in one molecule (COT-APD). The calculated results prove that COT-APD has a saddle-like configuration similar to that of other COT-type molecules. Each APD segment in COT-APD keeps the inherent aromaticity of the APD moiety. Compared with other COT-type molecules, COT-APD shows a narrower bandgap, which indicates the superiority of APD in bandgap regulation. Furthermore, four reversible reductive waves are observed in electrochemical characterizations, demonstrating the excellent electron-accepting capability of COT-APD.</p> ","PeriodicalId":93348,"journal":{"name":"Organic Materials","volume":"198 1","pages":""},"PeriodicalIF":0.0,"publicationDate":"2024-04-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140826971","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Diazananographene with Quadruple [5]Helicene Units: Synthesis, Optical Properties, and Supramolecular Assembly 具有四重 [5]苝单元的二氮杂三嗪：合成、光学性质和超分子组装
Organic Materials Pub Date : 2024-04-30 DOI: 10.1055/a-2291-8673
Xiao-Hui Ma, Jiang-Feng Xing, Ling Chai, Qing-Song Deng, Xuan-Wen Chen, Hai-Feng Su, Chao Li, Yuan-Zhi Tan
{"title":"Diazananographene with Quadruple [5]Helicene Units: Synthesis, Optical Properties, and Supramolecular Assembly","authors":"Xiao-Hui Ma, Jiang-Feng Xing, Ling Chai, Qing-Song Deng, Xuan-Wen Chen, Hai-Feng Su, Chao Li, Yuan-Zhi Tan","doi":"10.1055/a-2291-8673","DOIUrl":"https://doi.org/10.1055/a-2291-8673","url":null,"abstract":"<p>A helical diazananographene (<b>1</b>) was successfully synthesized by employing sterically hindered <i>t</i>-butyl groups to inhibit further dehydrocyclization of [5]helicene units. These <i>t</i>-butyl groups stabilized the conformation of [5]helicene units, thus resulting in three stable conformers of <b>1</b>, comprising a pair of enantiomers (<b>1</b>-(<i>P, P, P, P</i>) and <b>1</b>-(<i>M, M, M, M</i>)) and a mesomer (<b>1</b>-(<i>P, P, M, M</i>)). In comparison to its planar analogs, helical <b>1</b> exhibited broadened peaks in both its absorption and emission spectra, leading to an increase in the emission quantum yield from 0.3 to 0.6. The significantly enhanced radiative decay rate (<i>k</i>\u0000<sub>r</sub>) accounted for the increase in the quantum yield of <b>1</b>. Additionally, it was observed that the compound could be fully protonated upon the addition of an equivalent acid. Furthermore, <b>1</b> assembled into a chiral trimeric metallosupramolecular complex upon coordination with the Pd<sup>II</sup> units. Both protonated <b>1</b> and the metallosupramolecular complex exhibited an enhanced circular dichroic response. These findings revealed that the incorporation of a helical structure and pyridinic nitrogen-doping into the nanographene can allow the synthesis of responsive chiroptical graphenic materials, which could serve as fundamental components for constructing chiral hierarchical metallosupramolecular structures.</p> ","PeriodicalId":93348,"journal":{"name":"Organic Materials","volume":"58 1","pages":""},"PeriodicalIF":0.0,"publicationDate":"2024-04-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140827010","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Research Progress of β-Ketoenamine-Linked Covalent Organic Frameworks for Photocatalytic Hydrogen Evolution 用于光催化氢气发生的 β-酮胺连接共价有机框架的研究进展
Organic Materials Pub Date : 2024-04-29 DOI: 10.1055/a-2291-8578
Ping Xue, Mingyuan Li, Mi Tang, Zhengbang Wang, Chengliang Wang
{"title":"Research Progress of β-Ketoenamine-Linked Covalent Organic Frameworks for Photocatalytic Hydrogen Evolution","authors":"Ping Xue, Mingyuan Li, Mi Tang, Zhengbang Wang, Chengliang Wang","doi":"10.1055/a-2291-8578","DOIUrl":"https://doi.org/10.1055/a-2291-8578","url":null,"abstract":"<p>β-Ketoamide covalent organic frameworks (COFs), also named Tp-COFs, are considered to be a milestone material in the history of photocatalysts because of their excellent visible-light absorption, high crystallinity, ultra-high stability and structural diversity. In recent years, a large number of Tp-COFs and their composites have been successfully constructed based on molecular or composite engineering strategies, and exhibited splendid photocatalytic water splitting activity. In comparison with a composite strategy, the molecular engineering technique effectively avoids interface problems by designing and preparing frameworks at the molecular level. Therefore, it is necessary to timely summarize the construction of Tp-COF photocatalysts based on the molecular engineering strategy, so as to provide some theoretical basis and enlightenment for the subsequent development of high-performance Tp-COFs. Finally, the shortcomings and challenges of this technique and personal views on the further development of Tp-COFs are presented.</p>","PeriodicalId":93348,"journal":{"name":"Organic Materials","volume":"19 1","pages":""},"PeriodicalIF":0.0,"publicationDate":"2024-04-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140809033","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Pentacene to Octacene: The Limit of Fourfold TIPS-Ethynylation 五碳烯到八碳烯：四重 TIPS-乙炔化的极限
Organic Materials Pub Date : 2024-01-09 DOI: 10.1055/a-2241-0243
Nico Zeitter, Nikolai Hippchen, Philipp Baur, Tamara Verena Unterreiner, F. Rominger, Jan Freudenberg, U. Bunz
{"title":"Pentacene to Octacene: The Limit of Fourfold TIPS-Ethynylation","authors":"Nico Zeitter, Nikolai Hippchen, Philipp Baur, Tamara Verena Unterreiner, F. Rominger, Jan Freudenberg, U. Bunz","doi":"10.1055/a-2241-0243","DOIUrl":"https://doi.org/10.1055/a-2241-0243","url":null,"abstract":"Soluble acenes beyond hexacene are rare. Their sensitivity complicates isolation, purification and application in devices. To increase the stability of acenes, functionalization with trialkylsilylethynyl substituents prevents [4+4] dimerization and oxidation. At the same time such acenes are soluble and processible. Here we present the modular synthesis of fourfold TIPS-ethynylated pentacenes to octacenes and investigate their optical and redox properties, frontier orbital positions (CV, DFT calculations) as well as their stability in solution (UV/vis, NMR spectroscopy). We also investigated their magnetic properties as a function of acene length. Pentacene, hexacene and heptacene are sufficiently stable to serve as semiconductors in thin-film transistors - the octacene rapidly decays to its butterfly dimer evidence by time-dependent NMR spectroscopy and crystal structure analysis.","PeriodicalId":93348,"journal":{"name":"Organic Materials","volume":"26 1","pages":""},"PeriodicalIF":0.0,"publicationDate":"2024-01-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139443641","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Polyampholyte Hydrogels with pH-Dependent Swelling for Controlled Catch & Release of Model Dyes 随 pH 值变化而溶胀的聚酰胺水凝胶可控制模型染料的捕获和释放
Organic Materials Pub Date : 2023-12-13 DOI: 10.1055/a-2228-4757
Tolga Ceper, Supun Mohotti, Leon Lange, F. Schacher
{"title":"Polyampholyte Hydrogels with pH-Dependent Swelling for Controlled Catch & Release of Model Dyes","authors":"Tolga Ceper, Supun Mohotti, Leon Lange, F. Schacher","doi":"10.1055/a-2228-4757","DOIUrl":"https://doi.org/10.1055/a-2228-4757","url":null,"abstract":"Polyampholyte hydrogels with tunable charge are synthesized by a facile two-step approach including the free radical crosslinking copolymerization of tert-butoxycarbonylaminomethylacrylate (tBAMA) with N,Nˊ-Methylenebisacrylamide and subsequent deprotection. Thermal, photo- and redox-initiating methods were utilized in the synthesis of crosslinked PtBAMA and the resulting polymer networks swell during deprotection in a mixture of trifluoro acetic acid/water. While the crosslinked PtBAMA forms organogels in various organic solvents such as chloroform, acetone and DMSO, polydehydroalanine (PDha) networks after deprotection form hydrogels with pH-dependent swelling and oscillatory swelling/deswelling depending on pH value and salinity. The tunable charge of the developed hydrogels was employed for a catch & release platform controlled by pH, in which methylene blue as a cationic model was adsorbed at pH 11 and desorbed at pH 2, whereas methyl blue as an anionic model dye was adsorbed at pH 2 and desorbed at pH 11.","PeriodicalId":93348,"journal":{"name":"Organic Materials","volume":"145 6","pages":""},"PeriodicalIF":0.0,"publicationDate":"2023-12-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139006478","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Recent Advances of Covalent Organic Frameworks as Water Splitting Electrocatalysts 共价有机框架作为水分离电催化剂的最新进展
Organic Materials Pub Date : 2023-12-05 DOI: 10.1055/a-2222-7218
Y. Yusran, Jie Zhao, Fengqian Chen, Q. Fang
{"title":"Recent Advances of Covalent Organic Frameworks as Water Splitting Electrocatalysts","authors":"Y. Yusran, Jie Zhao, Fengqian Chen, Q. Fang","doi":"10.1055/a-2222-7218","DOIUrl":"https://doi.org/10.1055/a-2222-7218","url":null,"abstract":"Developing high performance, durable, yet low-lost catalyst for electrocatalytic water splitting technology has been a research priority to tackle the global energy crisis. In this regard, covalent organic frameworks (COFs) have received numerous attentions as promising water splitting electrocatalysts as they can provide an excellent platform for settlement of electrocatalytic active site, high porosity, and good stability. In this review, recent advance on the design and application of COFs for water electrolysis, that are hydrogen and oxygen evolution reaction (HER and OER) electrocatalysts are briefly discussed. Among them, both noble and non-noble metals containing COFs as well as metal-free COFs based electrocatalysts are elaborated. Furthermore, a brief perspective on development of COFs in the field of water splitting electrocatalysis is provided.","PeriodicalId":93348,"journal":{"name":"Organic Materials","volume":"122 27","pages":""},"PeriodicalIF":0.0,"publicationDate":"2023-12-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"138599609","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Progress of Polycyclic Boron-Doped Molecular Carbons 多环硼掺杂碳分子的研究进展
Organic Materials Pub Date : 2023-11-28 DOI: 10.1055/a-2213-1732
Liuzhong Yuan, Yue Wang, Chuandong Dou
{"title":"Progress of Polycyclic Boron-Doped Molecular Carbons","authors":"Liuzhong Yuan, Yue Wang, Chuandong Dou","doi":"10.1055/a-2213-1732","DOIUrl":"https://doi.org/10.1055/a-2213-1732","url":null,"abstract":"<p>Molecular carbons, namely molecular cutout of carbon materials, are of importance for understanding accurate structures of carbon allotropes and developing functional π-electron materials. Doping the boron atoms into π-conjugated skeletons of molecular carbons enables the construction of boron-doped molecular carbons (BMCs), further leading to new chemistry and attractive material systems, which are distinct from carbon-based and other heteroatom-doped molecular carbons. Herein, the bottom-up organic synthesis methodologies have been employed to synthesize BMCs that feature the boron atoms at the edge or in the center of π-skeletons. They have not only amazing topological structures and good stability but also intriguing photophysical and electronic properties. Moreover, they have sufficient Lewis acidity and can coordinate with Lewis bases to form Lewis acid–base complexes, which exhibit stimuli-responsive functions. Notably, some of these BMCs can be utilized in the fields of organic reactions, optical and electronic devices, as well as supramolecular chemistry and photothermal materials. In this short review, we aim to highlight the design and synthetic strategies of polycyclic BMCs, and their unique physical properties and practical applications.</p> ","PeriodicalId":93348,"journal":{"name":"Organic Materials","volume":"39 6","pages":""},"PeriodicalIF":0.0,"publicationDate":"2023-11-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"138512561","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
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