{"title":"Mapping the Side-Chain Length of Small-Molecule Acceptors towards the Optimal Hierarchical Morphology in Ternary Organic Solar Cells","authors":"Zichun Zhou, Shengjie Xu, Xiaozhang Zhu","doi":"10.1055/a-1472-7302","DOIUrl":"https://doi.org/10.1055/a-1472-7302","url":null,"abstract":"Abstract Using multiple light-absorbing materials to realize a broader and better absorption spectrum in multi-component organic photovoltaics has achieved significant success to obtain high power conversion efficiency. Meanwhile, the good materials combinations with matched electronic structure and proper blend morphology for charge generation and transport are of primary importance for implementation of the multi-component strategy. Hierarchical morphology has been clearly demonstrated to improve all performance parameters in ternary organic photovoltaics but shows strong dependence on the molecular structures. Here we develop four small-molecule electron acceptors with different alkyl chain lengths to find the optimal solution of alkyl chain towards the defined hierarchical morphology and carry out a clear and comprehensive investigation of the alkyl chain length effects on the structure–morphology–device performance relationships in ternary blends. There is a positive correlation between the power conversion efficiencies of the four ternary systems and their short-circuit current density parameters, manifesting the significance of distinguishing optimal alkyl side chain length of small-molecule electron acceptors for defined hierarchical morphology to afford efficient carrier generation. The non-optimal side chains would retard the BTR crystallization and make the PC71BM domain sizes incontrollable, leading to a morphology without a defined hierarchy. Such a detailed mapping of the alkyl side chain length of small-molecule electron acceptors provides new insight into the materials combinations for the next-step high-performance multi-component organic photovoltaics.","PeriodicalId":93348,"journal":{"name":"Organic Materials","volume":"03 1","pages":"191 - 197"},"PeriodicalIF":0.0,"publicationDate":"2021-04-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1055/a-1472-7302","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"47251885","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}
{"title":"Supramolecular Approaches for Taming the Chemo- and Regiochemistry of C60 Addition Reactions","authors":"Sebastian B. Beil, Max von Delius","doi":"10.1055/s-0041-1727182","DOIUrl":"https://doi.org/10.1055/s-0041-1727182","url":null,"abstract":"Abstract The chemo- and regioselective functionalization of fullerenes is a long-standing problem of organic synthesis. Over the past five years, this fundamental challenge has gained technological relevance, because studies on single bis-adduct isomers in new-generation solar cells have demonstrated that the widespread use of isomer mixtures leads to suboptimal power conversion efficiencies. Herein, we review recent work on supramolecular approaches for achieving chemo- and regioselective syntheses of multiply functionalized derivatives of C60.","PeriodicalId":93348,"journal":{"name":"Organic Materials","volume":"03 1","pages":"146 - 154"},"PeriodicalIF":0.0,"publicationDate":"2021-04-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1055/s-0041-1727182","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"42516727","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}
Marcus Richter, Michal Borkowski, Yubin Fu, E. Dmitrieva, A. Popov, Ji Ma, T. Marszalek, W. Pisula, Xinliang Feng
{"title":"Synthesis and Self-Assembly Behavior of Double Ullazine-Based Polycyclic Aromatic Hydrocarbons","authors":"Marcus Richter, Michal Borkowski, Yubin Fu, E. Dmitrieva, A. Popov, Ji Ma, T. Marszalek, W. Pisula, Xinliang Feng","doi":"10.1055/a-1472-6852","DOIUrl":"https://doi.org/10.1055/a-1472-6852","url":null,"abstract":"Abstract Polycyclic aromatic azomethine ylides (PAMY, 1) are versatile building blocks for the bottom-up synthesis of nitrogen-containing polycyclic aromatic hydrocarbons (N-PAHs). Although the chemistry of PAMY was already established few years ago, the cycloaddition of a double PAMY building block has not been reported so far. In this work, we demonstrate the first cycloaddition of a PAMY-dimer (6), which opens the access to three different alkyl ester-substituted N-PAHs with a laterally extended double ullazine scaffold (DU-1, DU-2 and DU-3). Interestingly, the cyclic voltammetry of DU-1–3 exhibited three reversible oxidation waves, which confirmed the electron-rich nature of the double ullazine scaffold. Furthermore, in situ spectroelectrochemistry study of ethylhexyl ester-substituted DU-3 revealed the formation of different cationic species with new absorption bands up to 1689 nm. Additionally, the influence of the attached substituents on the film formation and supramolecular organization in the thin films was investigated by polarized optical microscopy and grazing incidence wide-angle X-ray scattering.","PeriodicalId":93348,"journal":{"name":"Organic Materials","volume":"03 1","pages":"198 - 203"},"PeriodicalIF":0.0,"publicationDate":"2021-04-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1055/a-1472-6852","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"48111065","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}
{"title":"Oligofuran–Benzothiadiazole Co-oligomers: Synthesis, Optoelectronic Properties and Reactivity","authors":"Dror Ben Abba Amiel, Choongik Kim, Ori Gidron","doi":"10.1055/s-0041-1729853","DOIUrl":"https://doi.org/10.1055/s-0041-1729853","url":null,"abstract":"Abstract Donor–acceptor–donor (DAD) triad systems are commonly applied as active materials in ambipolar organic field-effect transistors, organic solar cells, and NIR-emitting organic light-emitting diodes. Often, these triads utilize oligothiophenes as donors, whereas their oxygen-containing analogs, oligofurans, are far less studied in this setup. Here we introduce a family of DAD triads in which the donors are oligofurans and the acceptor is benzothiadiazole. In a combined computational and experimental study, we show that these triads display optical bandgaps similar to those of their thiophene analogs, and that a bifuran donor is sufficient to produce emission in the NIR spectral region. The presence of a central acceptor unit increases the photostability of oligofuran-based DAD systems compared with parent oligofurans of the similar length.","PeriodicalId":93348,"journal":{"name":"Organic Materials","volume":"03 1","pages":"303 - 308"},"PeriodicalIF":0.0,"publicationDate":"2021-04-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1055/s-0041-1729853","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"43573040","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}
{"title":"High-Performance Ternary Organic Solar Cells Enabled by Synergizing Fullerene and Non-fullerene Acceptors","authors":"Yuanyuan Jiang, Xiaozhang Zhu","doi":"10.1055/a-1472-3989","DOIUrl":"https://doi.org/10.1055/a-1472-3989","url":null,"abstract":"Abstract With the development of the non-fullerene acceptors (NFAs), the use of ternary organic photovoltaic devices based on a fullerene acceptor and a NFA is now widespread, and the merits of both acceptor types can be fully utilized. However, the effective approach of enhancing device performance is adjusting the charge dynamics and the thin-film morphology of the active layer via introducing the second acceptor, which would significantly impact the open-circuit voltage, the short-circuit current, and the fill factor, thus strongly affecting device efficiency. The functions of the second acceptor in a ternary organic solar cell with a fullerene acceptor and a NFA are summarized here. These include a broader absorption spectrum; formation of a cascade energy level or energy transfer; modified thin-film morphology including phase separation, effects on crystallinity, size, and purity of domain; and vertical distribution along with improved charge dynamics like exciton dissociation and charge transport, collection, and recombination. Then, we discuss the hierarchical morphology in ternary solar cells, which may benefit device performance, and the outlook of the ternary device.","PeriodicalId":93348,"journal":{"name":"Organic Materials","volume":"03 1","pages":"254 - 276"},"PeriodicalIF":0.0,"publicationDate":"2021-03-31","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1055/a-1472-3989","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"47265755","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}
{"title":"Strategies for Pore-Diameter Control in Mesoporous Carbons Derived from Organic Self-Assembly Processes","authors":"S. Naumann","doi":"10.1055/a-1458-5109","DOIUrl":"https://doi.org/10.1055/a-1458-5109","url":null,"abstract":"Abstract Soft-templating techniques have greatly facilitated access to (ordered) mesoporous carbon materials. A key strength of these approaches is that the resulting material can be shaped by a multitude of parameters – rendering soft-templating inherently versatile regarding features such as pore arrangement or pore sizes. Nonetheless, rational manipulation of pore sizes/diameters, let alone a systematic variation thereof, remains a formidable challenge with high relevance for research fields as diverse as catalysis, sensing or energy storage and conversion. Thus, this Short Review aims to provide a structured account of the most frequently employed strategies to impact mesopore diameters in carbon materials derived via soft-templating. 1. Introduction 2. Carbonization Temperature 3. Stoichiometry 4. Swelling Agents 5. Design of Polymeric SDAs/Templates 6. Conclusions and Outlook","PeriodicalId":93348,"journal":{"name":"Organic Materials","volume":"03 1","pages":"283 - 294"},"PeriodicalIF":0.0,"publicationDate":"2021-03-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1055/a-1458-5109","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"44164434","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}
{"title":"Chain-End Effect for Intermediate Water Formation of Poly(2-Methoxyethyl Acrylate)","authors":"S. Nishimura, T. Ueda, D. Murakami, M. Tanaka","doi":"10.1055/a-1441-8239","DOIUrl":"https://doi.org/10.1055/a-1441-8239","url":null,"abstract":"Abstract Intermediate water (IW), which is formed not only by biocompatible polymers such as poly(2-methoxyethyl acrylate) (PMEA), but also by biomacromolecules, plays a key role in determining the biocompatibility of synthetic polymers. In this study, we compare the well-defined linear and cyclic PMEA using differential scanning calorimetry and atomic force microscopy. This study aims to clarify the role of the chain-end effect in IW formation to establish design guidelines for biomaterials.","PeriodicalId":93348,"journal":{"name":"Organic Materials","volume":"03 1","pages":"214 - 220"},"PeriodicalIF":0.0,"publicationDate":"2021-03-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1055/a-1441-8239","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"41322549","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}
{"title":"Asymmetric Organocatalysis with Chiral Covalent Organic Frameworks","authors":"Songjie Yu, Liang Cheng, Li Liu","doi":"10.1055/a-1400-5581","DOIUrl":"https://doi.org/10.1055/a-1400-5581","url":null,"abstract":"Abstract Inspired by Mother Nature, the use of chiral covalent organic frameworks as heterogeneous asymmetric organocatalysts has arisen over the last decade as a new method in enantioselective synthesis. In this Short Review, sophisticated design of these polymeric materials and their application in asymmetric organocatalysis will be discussed.","PeriodicalId":93348,"journal":{"name":"Organic Materials","volume":"03 1","pages":"245 - 253"},"PeriodicalIF":0.0,"publicationDate":"2021-02-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1055/a-1400-5581","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"43939142","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}
{"title":"Controlled Ring-Opening Polymerization of O-Carboxyanhydrides to Synthesize Functionalized Poly(α-Hydroxy Acids)","authors":"Xiaoqian Wang, A. L. Chin, R. Tong","doi":"10.1055/s-0040-1722698","DOIUrl":"https://doi.org/10.1055/s-0040-1722698","url":null,"abstract":"Abstract Poly(α-hydroxy acids), as a family of biodegradable polyesters, are valuable materials due to their broad applications in packaging, agriculture, and biomedical engineering. Herein we highlight and explore recent advances of catalysts in controlled ring-opening polymerization of O-carboxyanhydrides towards functionalized poly(α-hydroxy acids), especially metal catalyst-mediated controlled polymerization. Limitations of current polymerization strategies of O-carboxyanhydrides are discussed. Introduction Organocatalysts for O-Carboxyanhydride Polymerization Metal Catalysts for O-Carboxyanhydride Polymerization Stereoselective and Stereosequence-Controlled Polymerization of O-Carboxyanhydrides Conclusions and Outlook","PeriodicalId":93348,"journal":{"name":"Organic Materials","volume":"03 1","pages":"041 - 050"},"PeriodicalIF":0.0,"publicationDate":"2021-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1055/s-0040-1722698","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"46387394","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}
Organic MaterialsPub Date : 2021-01-01Epub Date: 2021-06-18DOI: 10.1055/s-0041-1730899
Sinu C Rajappan, Olav Vestrheim, Mona Sharafi, Jianing Li, Severin T Schneebeli
{"title":"Carbonyl-to-Alkyne Electron Donation Effects in up to 10-nm-Long, Unimolecular Oligo(<i>p</i>-phenylene ethynylenes).","authors":"Sinu C Rajappan, Olav Vestrheim, Mona Sharafi, Jianing Li, Severin T Schneebeli","doi":"10.1055/s-0041-1730899","DOIUrl":"10.1055/s-0041-1730899","url":null,"abstract":"<p><p>We synthesized some of the longest unimolecular oligo(<i>p</i>-phenylene ethynylenes) (OPEs), which are fully substituted with electron-withdrawing ester groups. An iterative convergent/divergent (a.k.a. iterative exponential growth - IEG) strategy based on Sonogashira couplings was utilized to access these sequence-defined macromolecules with up to 16 repeating units and 32 ester substituents. The carbonyl groups of the ester substituents interact with the triple bonds of the OPEs, leading to (i) unusual, angled triple bonds with increased rotational barrier, (ii) enhanced conformational disorder, and (iii) associated broadening of the UV/Vis absorption spectrum. Our results demonstrate that fully air-stable, unimolecular OPEs with ester groups can readily be accessed with IEG chemistry, providing new macromolecular backbones with unique geometrical, conformational, and photophysical properties.</p>","PeriodicalId":93348,"journal":{"name":"Organic Materials","volume":"3 2","pages":"337-345"},"PeriodicalIF":0.0,"publicationDate":"2021-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1055/s-0041-1730899","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"39405230","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}