Journal of Polymer Science, volume 59, issue 24, pages 3150-3160

Living ring‐opening metathesis polymerization of norbornenes bay ‐functionalized perylene diimides

Publication type: Journal Article
Publication date: 2021-10-14
scimago Q1
SJR: 0.827
CiteScore: 6.3
Impact factor: 3.9
ISSN: 00223832, 15426238, 26424150, 26424169
Materials Chemistry
Physical and Theoretical Chemistry
Polymers and Plastics
Abstract
Ring-opening metathesis polymerization (ROMP)-derived poly(oxanorbornene imide)s bearing bay-linked mono-alkoxy-M1 and 1,7-di-alkoxy M2 functionalized perylene diimides (PDIs) were synthesized using Grubb's third (G3) and Hoveyda-Grubbs second generation (HG2) ruthenium-alkylidene metathesis initiators. The mono-alkoxy-derived PDI-based non-ladderphane polymer polyM1 displayed 67% to 77% of the trans olefin content in the polymer chain depending on the initiator used for the polymerization. When using the symmetrical 1,7-di-alkoxy-derived PDI-based polymer polyM2 having the ladderphane type-structure, this displayed a significant amount of cis and trans olefin contents in the polymer chains, irrespective of the type of initiators used for the polymerization. ROMP of both monomers M1 and M2 proceeded in a well-controlled manner with a linear dependence of molecular weight on the monomer/initiator ratio using G3 as initiator. Optical properties of the ladderphane-based polyM2 and non-ladderphane-based polyM1 were characterized in both solution and the film state. X-ray diffraction (XRD) analysis for all the polymers showed significant π-stacking in the thin film state with ordered molecular packing and closer values of d-spacing for both polyM1 and polyM2. Film morphology examined by AFM elucidated homogenous smooth polymer surface for both polymers in general, but with some irregularities observed for polyM1. In addition, CV analysis revealed both polymers could be good candidates as electron-accepting materials, with excellent film-forming ability, and thermal stability.
Found 51
By date By citations
Royal Society of Chemistry (RSC)
Perylene diimide based non-fullerene acceptors: top performers and an emerging class featuring N-annulation
Sharma V., Koenig J.D., Welch G.C.
Journal of Materials Chemistry A scimago Q1 wos Q1 , 
2021-02-15,  citations by CoLab: 77 ,  Abstract  
This perspective showcases new materials designs for perylene diimide based non-fullerene acceptors towards high performance photovoltaic devices.
MDPI
Recent Advances in Perylene Diimide-Based Active Materials in Electrical Mode Gas Sensing
Ali S., Gupta A., Shafiei M., Langford S.J.
Chemosensors scimago Q2 wos Q1 Open Access , 
2021-02-01,  citations by CoLab: 29 ,  PDF,  Abstract  
This review provides an update on advances in the area of electrical mode sensors using organic small molecule n-type semiconductors based on perylene. Among small organic molecules, perylene diimides (PDIs) are an important class of materials due to their outstanding thermal, chemical, electronic, and optical properties, all of which make them promising candidates for a wide range of organic electronic devices including sensors, organic solar cells, organic field-effect transistors, and organic light-emitting diodes. This is mainly due to their electron-withdrawing nature and significant charge transfer properties. Perylene-based sensors of this type show high sensing performance towards various analytes, particularly reducing gases like ammonia and hydrazine, but there are several issues that need to be addressed including the selectivity towards a specific gas, the effect of relative humidity, and operating temperature. In this review, we focus on the strategies and design principles applied to the gas-sensing performance of PDI-based devices, including resistive sensors, amperometric sensors, and operating at room temperature. The device properties and sensing mechanisms for different analytes, focusing on hydrazine and ammonia, are studied in detail, and some future research perspectives are discussed for this promising field. We hope the discussed results and examples inspire new forms of molecular engineering and begin to open opportunities for other rylene diimide classes to be applied as active materials.
Wiley
Perylene Diimide‐Based Conjugated Polymers for All‐Polymer Solar Cells
Shi Q., Wu J., Wu X., Peng A., Huang H.
Chemistry - A European Journal scimago Q1 wos Q2 , 
2020-08-11,  citations by CoLab: 35 ,  Abstract  
In recent decades, non-fullerene acceptors (NFAs) are undergoing rapid development and emerging as a hot area in the field of organic solar cells. Among the high-performance non-fullerene acceptors, aromatic diimide-based electron acceptors remain to be highly promising systems. This review discusses the important progress of perylene diimide (PDI)-based polymers as non-fullerene acceptors in all-polymer solar cells (all-PSCs) since 2014. The relationship between structure and property, matching aspects between donors and acceptors, and device fabrications are unveiled from a synthetic chemist perspective.
American Chemical Society (ACS)
Regioisomerically Pure 1,7-Dicyanoperylene Diimide Dimer for Charge Extraction from Donors with High Electron Affinities
Pettipas R.D., Radford C.L., Kelly T.L.
ACS Omega scimago Q2 wos Q2 Open Access , 
2020-06-29,  citations by CoLab: 6 ,  PDF,  Abstract  
Perylene diimide (PDI) has attracted widespread interest as an inexpensive electron acceptor for photovoltaic applications; however, overcrystallization in the bulk heterojunction typically leads to low device performance. Recent work has addressed this issue by forming bay-linked PDI dimers and oligomers, where the steric bulk of adjacent PDI units forces the molecule to adopt a nonplanar structure. This disrupts the molecular packing and limits domain sizes in the bulk heterojunction. Unfortunately, the introduction of electron-donating/-withdrawing groups in the bay region is also the best way to fine-tune the frontier molecular orbitals (FMOs) of PDI, which is highly desirable from a device optimization standpoint. This competition for the bay region has made it difficult for PDI to keep pace with other non-fullerene acceptors. Here, we report the synthesis of regioisomerically pure 1,7-dicyanoperylene diimide and its dimerization through an imide linkage. We show that this is an effective strategy to tune the energies of the FMOs while simultaneously suppressing overcrystallization in the bulk heterojunction. The resulting acceptor has a low LUMO energy of -4.2 eV and is capable of accepting photogenerated electrons from donor polymers with high electron affinities, even when conventional acceptors such as PDI, PC71BM, and ITIC cannot.
American Chemical Society (ACS)
Ru-Catalyzed, cis-Selective Living Ring-Opening Metathesis Polymerization of Various Monomers, Including a Dendronized Macromonomer, and Implications to Enhanced Shear Stability
Song J., Peterson G.I., Bang K., Ahmed T.S., Sung J., Grubbs R.H., Choi T.
Journal of the American Chemical Society scimago Q1 wos Q1 , 
2020-05-11,  citations by CoLab: 33 ,  Abstract  
An unsaturated polymer's cis/trans-olefin content has a significant influence on its properties. For polymers obtained by ring-opening metathesis polymerization (ROMP), the cis/trans-olefin content can be tuned by using specific catalysts. However, cis-selective ROMP has suffered from narrow monomer scope and lack of control over the polymerization (giving polymers with broad molecular weight distributions and prohibiting the synthesis of block copolymers). Herein, we report the versatile cis-selective controlled living ROMP of various endo-tricyclo[4.2.2.02,5]deca-3,9-diene and various norbornene derivatives using a fast-initiating dithiolate-chelated Ru catalyst. Polymers with cis-olefin content as high as 99% could be obtained with high molecular weight (up to Mn of 105.1 kDa) and narrow dispersity (
MDPI
Development of Perylene-Based Non-Fullerene Acceptors through Bay-Functionalization Strategy
Fujimoto K., Takahashi M., Izawa S., Hiramoto M.
Materials scimago Q2 wos Q2 Open Access , 
2020-05-06,  citations by CoLab: 26 ,  PDF,  Abstract  
Perylene has had a tremendous impact in the history of material research for the molecular semiconductors. Among numerous derivatives of this polyaromatic hydrocarbon, perylene diimide (PDI) represents a promising class of organic materials envisioned as non-fullerene acceptors (NFAs) for the practical organic photovoltaic (OPV) applications due to their enhanced photo- and thermal stability and remarkably high electron affinity, some of which realize band-like transport properties. The present review guides some of the representative achievements in the development of rationally designed PDI systems, highlighting synthetic methodologies based on bay-functionalization strategies for creating well-designed molecular nanostructures and structure-performance relationship of perylene-based small molecular acceptors (SMAs) for the photovoltaic outcomes.
Royal Society of Chemistry (RSC)
Aromatic imide/amide-based organic small-molecule emitters for organic light-emitting diodes
Qin Y., Li G., Qi T., Huang H.
Materials Chemistry Frontiers scimago Q1 wos Q1 , 
2020-04-17,  citations by CoLab: 54 ,  Abstract  
Aromatic imide/amide-based organic small molecules as emitters in organic light-emitting diodes have caught increasing attention. This study summarized their advances in terms of device performance and molecular design rules over the past 20 years.
MDPI
Perylene Diimide-Based Fluorescent and Colorimetric Sensors for Environmental Detection
Chen S., Xue Z., Gao N., Yang X., Zang L.
Sensors scimago Q1 wos Q2 Open Access , 
2020-02-09,  citations by CoLab: 64 ,  PDF,  Abstract  
Perylene tetracarboxylic diimide (PDI) and its derivatives exhibit excellent thermal, chemical and optical stability, strong electron affinity, strong visible-light absorption and unique fluorescence on/off features. The combination of these features makes PDIs ideal molecular frameworks for development in a broad range of sensors for detecting environmental pollutants such as heavy metal ions (e.g., Cu2+, Cd2+, Hg2+, Pd2+, etc.), inorganic anions (e.g., F−, ClO4−, PO4−, etc.), as well as poisonous organic compounds such as nitriles, amines, nitroaromatics, benzene homologues, etc. In this review, we provide a comprehensive overview of the recent advance in research and development of PDI-based fluorescent sensors, as well as related colorimetric and multi-mode sensor systems, for environmental detection in aqueous, organic or mixed solutions. The molecular design of PDIs and structural optimization of the sensor system (regarding both sensitivity and selectivity) in response to varying analytes are discussed in detail. At the end, a perspective summary is provided covering both the key challenges and potential solutions for the future development of PDI-based optical sensors.
Springer Nature
Recyclable heterogeneous palladium-catalyzed carbon–carbon coupling polycondensations toward highly purified conjugated polymers
Zou F., Yao F., Liu L., Cai M.
Journal of Polymer Research scimago Q2 wos Q3 , 
2019-12-03,  citations by CoLab: 88 ,  Abstract  
Conjugated polymers are usually synthesized by homogeneous palladium complexes-catalyzed Heck, Suzuki, and Stille coupling reactions, which suffer from the non- recyclability of expensive palladium catalysts and palladium contamination of the desired polymer due to palladium leaching. In order to overcome these drawbacks, a bidentate phosphino-modified magnetic nanoparticles-anchored palladium complex (PdCl2-Fe3O4@SiO2-2P) as a clean and efficient heterogeneous catalyst for the carbon–carbon coupling polycondensations was developed in present work. The PdCl2-Fe3O4@SiO2-2P catalyst exhibited an enhanced catalytic activity for Heck, Suzuki, and Stille coupling polymerizations, as compared with the most commonly used homogeneous Pd(PPh3)4. Moreover, this heterogeneous palladium catalyst showed advantage of much less palladium impurity (below 13 ppm) in the isolated polymers. Importantly, PdCl2-Fe3O4@SiO2-2P can facilely be separated from the reaction products and recovered by using an external magnetic field, and recycled at least eight times with almost consistent catalytic activity.
American Chemical Society (ACS)
Examining the Effects of Monomer and Catalyst Structure on the Mechanism of Ruthenium-Catalyzed Ring-Opening Metathesis Polymerization
Wolf W.J., Lin T., Grubbs R.H.
Journal of the American Chemical Society scimago Q1 wos Q1 , 
2019-10-25,  citations by CoLab: 70 ,  Abstract  
The mechanism of Ru-catalyzed ring-opening metathesis polymerization (ROMP) is studied in detail using a pair of third generation ruthenium catalysts with varying sterics of the N-heterocyclic carbene (NHC) ligand. Experimental evidence for polymer chelation to the Ru center is presented in support of a monomer-dependent mechanism for polymerization of norbornene monomers using these fast-initiating catalysts. A series of kinetic experiments, including rate measurements for ROMP, rate measurements for initiation, monomer-dependent kinetic isotope effects, and activation parameters were useful for distinguishing chelating and nonchelating monomers and determining the effect of chelation on the polymerization mechanism. The formation of a chelated metallacycle is enforced by both the steric bulk of the NHC and by the geometry of the monomer, leading to a ground-state stabilization that slows the rate of polymerization and also alters the reactivity of the propagating Ru center toward different monomers in copolymerizations. The results presented here add to the body of mechanistic work for olefin metathesis and may inform the continued design of catalysts for ROMP to access new polymer architectures and materials.
Elsevier
7, 8-Dichlorobenzo[ghi]perylenetriimide: A versatile synthon for bay-substituted π-extended perylene dyes
Li L., Zhu J., Hong Y., Li M., Xiao W., Lin M.
Dyes and Pigments scimago Q2 wos Q1 , 
2019-08-01,  citations by CoLab: 10 ,  Abstract  
Bay-substituted perylene diimide (PDI) dyes are a subject of great interest in both industrial and academic domains in the past decades. As important laterally extended derivatives of PDI dyes, benzo[ghi]perylenetriimides (BPTIs) have attracted much attention as non-fullerene acceptors, but their scope for applications has been limited by the lack of substitutions at the remaining two bay positions. Herein, we reported a facile synthesis of a novel, highly valuable synthon, 7, 8-dichlorobenzo[ghi]perylenetriimide (2), with two easy leaving chlorine groups at the remaining bay area, which can be further substituted by other functionalized groups through various synthetic strategies. Due to foreseeable applications of core-functionalized BPTIs, this unique synthon is anticipated to open up a fresh ground for optoelectronic materials.
American Chemical Society (ACS)
Perylene Bisimide Dyes with up to Five Independently Introduced Substituents: Controlling the Functionalization Pattern and Photophysical Properties Using Regiospecific Bay Substitution
Dubey R.K., Eustace S.J., van Mullem J.S., Sudhölter E.J., Grozema F.C., Jager W.F.
Journal of Organic Chemistry scimago Q2 wos Q1 , 
2019-07-12,  citations by CoLab: 31 ,  Abstract  
We report herein a versatile and user-friendly synthetic methodology based on sequential functionalization that enables the synthesis of previously unknown perylene bisimide (PBI) dyes with up to five different substituents attached to the perylene core (e.g., compound 15). The key to the success of our strategy is a highly efficient regiospecific 7-mono- and 7,12-di-phenoxy bay substitution at the “imide-activated” 7- and 12-bay positions of 1,6,7,12-tetrachloroperylene monoimide diester 1. The facile subsequent conversion of the diester groups into an imide group resulted in novel PBIs (e.g., compound 14) with two phenoxy substituents specifically at the 7- and 12-bay positions. This conversion led to the activation of C-1 and C-6 bay positions, and thereafter, the remaining two chlorine atoms were substituted to obtain tetraphenoxy-PBI (compound 15) that has two different imide and three different bay substituents. The methodology provides excellent control over the functionalization pattern, which enables the synthesis of various regioisomeric pairs bearing the same bay substituents. Another important feature of this strategy is the high sensitivity of HOMO–LUMO energies and photoinduced charge transfer toward sequential functionalization. As a result, systematic fluorescence on–off switching has been demonstrated upon subsequent substitution with the electron-donating 4-methoxyphenoxy substituent.
Elsevier
Substitution effects on NIR-absorbing Perylene Diimide based on DFT calculation
Li H., Meng J., Sun X.
Inorganic Chemistry Communication scimago Q1 wos Q1 , 
2019-07-01,  citations by CoLab: 8 ,  Abstract  
Two novel PDI derivatives with bay area functionalization and thionation of the carbonyls, respectively, were designed and their absorption was evaluated by DFT calculation, which predicted to be in the NIR region that is desired for potential application. The effect of the substitutions on the band gap (BG) narrowing and spectral shift was disclosed accordingly. In particular, electron donating group decorated at the bay positions mainly causes HOMO energy level rise up, while thionation contributes greatly to decreased LUMO energy. The significance of imine group for bay functionalization was also clarified, which is essential to the formation of conjugation between substituents and PDI framework to shift LUMO positively.
Royal Society of Chemistry (RSC)
Progress in the synthesis of perylene bisimide dyes
Nowak-Król A., Würthner F.
Organic Chemistry Frontiers scimago Q1 wos Q1 , 
2019-03-07,  citations by CoLab: 303 ,  Abstract  
Rapid progress in the synthesis of perylene bisimide dyes gave an old scaffold new life.
MDPI
Grubbs’ and Schrock’s Catalysts, Ring Opening Metathesis Polymerization and Molecular Brushes—Synthesis, Characterization, Properties and Applications
Choinopoulos I.
Polymers scimago Q1 wos Q1 Open Access , 
2019-02-11,  citations by CoLab: 66 ,  PDF,  Abstract  
In this review, molecular brushes and other macromolecular architectures bearing a bottlebrush segment where the main chain is synthesized by ring opening metathesis polymerization (ROMP) mediated by Mo or Ru metal complexes are considered. A brief review of metathesis and ROMP is presented in order to understand the problems and the solutions provided through the years. The synthetic strategies towards bottlebrush copolymers are demonstrated and each one discussed separately. The initiators/catalysts for the synthesis of the backbone with ROMP are discussed. Syntheses of molecular brushes are presented. The most interesting properties of the bottlebrushes are detailed. Finally, the applications studied by different groups are presented.
Found 8
By date By citations
Autonomous Non-profit Organization Editorial Board of the journal Uspekhi Khimii
Hoveyda-Grubbs type complexes with ruthenium-pnictogen/halcogen/halogen coordination bond. Synthesis, catalytic activity, applications.
Antonova Alexandra S., Zubkov Fedor I.
Russian Chemical Reviews scimago Q1 wos Q1 Open Access , 
2024-08-30,  citations by CoLab: 1 ,  PDF,  Abstract  
Catalytic olefin metathesis using Hoveyda-Grubbs type ruthenium complexes is a powerful tool for creating complex molecules possessing a variety of practically useful properties. This method is also applied for obtaining modern polymer materials from low-demand petroleum products. Among all ruthenium complexes containing five- or six-membered chelate rings, the commercially available HG-II catalyst is the most common. In addition, other Hoveyda-Grubbs type complexes, which include a Het→Ru donor–acceptor bond in the chelate ring, often exhibit metathesis activity equal to or superior to that of HG-II. This review considers second-generation N-heterocyclic ruthenium carbene Hoveyda-Grubbs type complexes with donor–acceptor bonds such as O→Ru, S→Ru, Se→Ru, N→Ru, P→Ru and Hal→Ru in the chelate ring. Methods of preparation, analysis of stability and catalytic activity of such complexes are compared, and examples of the application of these organometallic ruthenium derivatives in the synthesis of practically relevant products are provided. The literature from 2010 to 2023 is summarized, making this review useful for a broad audience of chemists working in heterocyclic and organometallic chemistry, as well as practitioners involved in the production of catalysts and polymers.The bibliography includes 174 references.
Royal Society of Chemistry (RSC)
Bridging of Poly(Acetylene)s and PEG-Modified Poly(Olefin)s Through Ring-Opening Metathesis Copolymerization (ROMCP)
Kumar Podiyanachari S., Barłóg M., Al-Hashimi M., Bazzi H.S.
Polymer Chemistry scimago Q1 wos Q2 , 
2024-05-09,  citations by CoLab: 0 ,  Abstract  
Amphiphilic copolymers of highly conjugated poly(acetylene)s and poly(ethylene glycol)-functionalized perylene diimide (PEG750-PDI)-incorporated poly(olefin)s have been synthesized via one-pot tandem cyclopolymerization and ring-opening metathesis copolymerization (ROMCP) methodologies. Both di- and tri-block...
AIP Publishing
Physical mechanism on ladderphane copolymers with electron localization and phonon delocalization for capacitive energy storage
Wu Y., Sun M.
Applied Physics Letters scimago Q1 wos Q2 , 
2023-10-09,  citations by CoLab: 0 ,  Abstract  
In this article, the properties of trapezoidal polymer PSBNP-co-PTNI for capacitive energy storage are investigated theoretically, stimulated by the recent experimental reports [Chen et al., Nature 615, 62 (2023)]. The flatband structures of PSBNP-co-PTNI copolymer reveal that very large effective mass of electron results in Anderson electron localization and then small electric conductance. The TNI doping significantly decreases optical absorption in an ultraviolet region, which can significantly suppress photocurrent. Raman spectrum demonstrates that phonon Debye temperature can be significantly decreased, due to the U-process of phonon scattering by TNI doping, and then results in the phonon delocalization, and then the large thermal conductivity and thermal capacity. The simultaneous regulations on decreasing electric conductivity and on increasing thermal conductivity can significantly increase the ability of capacitive energy storage. The unit-length dependent thermal electric current manifests that the thermal electric current can be significantly decreased by slightly increase in length of copolymer. Overall, our research contributes to the understanding of the impact of TNI doping on the energy storage properties of the polymer and provides a valuable reference for future research focused on polymer energy storage.
Royal Society of Chemistry (RSC)
Synthesis of polynorbornadienes by ring-opening metathesis polymerization and their saturated derivatives bearing various ester groups and carboxyl groups
Lin X., Shi J., Niwayama S.
RSC Advances scimago Q1 wos Q2 Open Access , 
2023-01-24,  citations by CoLab: 6 ,  PDF,  Abstract  
Polymer libraries were synthesized in a controlled living manner from half-esters efficiently prepared by the selective monohydrolysis of symmetric diesters.
Royal Society of Chemistry (RSC)
Poly(oxanorbornene)s bearing triphenylphosphonium and PEGylated zinc(ii) phthalocyanine with boosted photobiological activity and singlet oxygen generation
Ahmetali E., Galstyan A., Süer N.C., Eren T., Şener M.K.
Polymer Chemistry scimago Q1 wos Q2 , 
2023-01-01,  citations by CoLab: 5 ,  Abstract  
Poly(oxanorbornene)s bearing TPP and PEGylated ZnPc with varying compositions have been synthesized. Thus, highest reported singlet oxygen generation for a Pc derivative in water (ΦΔ = 0.93) and excellent biological activity have been accomplished.
Royal Society of Chemistry (RSC)
Organic Memory Device and Synaptic Simulation Based on Indacenodithienothiophene (IDTT) Copolymers with Improved Planarity
Feng Z., Comi M., Ren Y., Sredojevic D.N., Attar S.S., Yang J., Wang Z., Chen R., Han S., Al-Hashimi M., Zhou Y.
Journal of Materials Chemistry C scimago Q1 wos Q1 , 
2022-10-14,  citations by CoLab: 6 ,  Abstract  
Utilization of organic semiconductors in the memory devices presents the advantages of molecular designability and flexibility. Here, we present the comparison of three indacenodithieno[3,2-b]thiophene (IDTT) based π-conjugated polymers via copolymerization...
Royal Society of Chemistry (RSC)
Molecular strategy towards ROMP-derived hyperbranched poly(olefin)s featuring various π-bridged perylene diimides
Barłóg M., Podiyanachari S.K., Attar S., Sredojević D.N., Bazzi H.S., Al-Hashimi M.
Polymer Chemistry scimago Q1 wos Q2 , 
2022-10-05,  citations by CoLab: 2 ,  Abstract  
Synthesis of ring-opening metathesis polymerization (ROMP)-derived highly conjugated chromophore functional hyperbranched polymers opens up new possibilities for obtaining functional conjugated macromolecules with novel photophysical and morphological properties.
Royal Society of Chemistry (RSC)
POSS-containing polynorbornene with pendant perylene diimide: from a unique supramolecular structure to tunable luminescence properties
Liu J., Gao S., Zhang X., Feng Y., Wu H., Chen Z., Bermeshev M.V., Ren X.
Journal of Materials Chemistry C scimago Q1 wos Q1 , 
2022-05-05,  citations by CoLab: 2 ,  Abstract  
The introduction of POSS cages leads to PDI-functionalized polynorbornene changing from a lamellar structure to a hexagonal columnar structure with tunable luminescence properties.

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