- Alkyl- and aryl-substituted benzo[ghi]perylenetriimides: Synthesis, characterization and comparison of electrochemical and spectroscopic properties
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Benzo[ghi]peryleneimides constitute a unique class of fluorescent perylene dyes which possesses great synthetic diversity due to the presence of a large number of reactive active sites (availability of third imide region). Taking advantage of this additio
- Viswanath, Lakshmi C. Kasi,Bernhardt, Jeremy,Kumar Gnanasekaran, Krishna,Want, Colton,Frank, Joshua,Faulkner, Jantzen,Krishnan, Sadagopan
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- Fluorescent water-soluble probes based on dendritic PEG substituted perylene bisimides: Synthesis, photophysical properties, and live cell images
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Water-soluble dyes based on dendritic polyethylene glycol (PEG)-substituted perylene bisimides were designed and synthesised. According to the distribution of hydrophilic dendritic PEGs, these dyes can be divided into two classes: (I) head-tail structured
- Liu, Hongmei,Wang, Yongli,Liu, Chenghui,Li, Hongxia,Gao, Baoxiang,Zhang, Licui,Bo, Fuli,Bai, Qianqian,Ba, Xinwu
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- Self-Assembled Perylene Bisimide-Cored Trigonal Prism as an Electron-Deficient Host for C60and C70Driven by "like Dissolves Like"
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Poor processability of fullerenes is a major remaining drawback for them to be studied monomolecularly and to find real-life applications. One of the strategies to tackle this problem is to encapsulate them within a host, which is however quite often, accompanied by significant alteration of their physical/chemical properties as encountered in chemical modification. To minimize the effect, an electron-deficient entities-based, dissolvable, and fluorescence active supramolecular host was designed and constructed via coordination-driven self-assembly of o-tetrapyridyl perylene bisimide (PBI) with cis-(PEt3)2Pt(OTf)2. The trigonal prism 1 possesses a trigonal-prismatic inner cavity with 14.7 ? as the diameter of its inscribed circle. Host-guest chemistry investigations revealed that both C60 and C70 could be quantitatively encapsulated by the host in a 1:1 ratio. Further studies demonstrated that the produced host-guest complex 1a?C70 is significantly more stable than 1a?C60, allowing complete transformation of the latter to the former and separation of C70 from its mixture with C60. The fullerenes in the inclusion state could rotate freely within the cavity. Electrochemistry and spectroscopy studies disclosed that the encapsulation of the guests shows little effect upon the reduction of the host and its fluorescence properties. Thus, "like dissolves like"is believed to be the main driving force for the formation of the host-guest complexes. Moreover, the host and host-guest complexes can be fabricated into monomolecular membranes using the conventional Langmuir-Blodgett technique. We propose that these unique host-guest complexes could be used as model ensembles for further studies of the physical/chemical properties of fullerenes in both single molecular and 2D membrane states. In addition, their reversible four-electron reduction property may allow them to find applications in photo/electrocatalysis, organic electronics, etc.
- Chang, Xingmao,Fang, Yu,Lin, Simin,Liu, Kaiqiang,Shang, Congdi,Stang, Peter J.,Wang, Gang,Wang, Zhaolong
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- Energy and electron transfer from fluorescent mesostructured organosilica framework to guest dyes
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Energy and electron transfer from frameworks of nanoporous or mesostructured materials to guest species in the nanochannels have been attracting much attention because of their increasing availability for the design and construction of solid photofunction
- Mizoshita, Norihiro,Yamanaka, Ken-Ichi,Hiroto, Satoru,Shinokubo, Hiroshi,Tani, Takao,Inagaki, Shinji
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- Intersystem Crossing and Triplet-State Property of Anthryl- And Carbazole-[1,12]fused Perylenebisimide Derivatives with a Twisted π-Conjugation Framework
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Heavy atom-free triplet photosensitizers (PSs) are particularly of interest concerning both fundamental photochemistry study and practical applications. However, achieving efficient intersystem crossing (ISC) in planar heavy atom-free aromatic organic compounds is challenging. Herein, we demonstrate that two perylenebisimide (PBI) derivatives with anthryl and carbazole moieties fused at the bay position, showing twisted π-conjugation frameworks and red-shifted UV-vis absorption as compared to the native PBI chromophore (by 75-1610 cm-1), possess efficient ISC (singlet oxygen quantum yield: φΔ = 85%) and a long-lived triplet excited state (τT = 382 μs in fluid solution and τT = 4.28 ms in solid polymer film). Femtosecond transient absorption revealed ultrafast intramolecular charge-transfer (ICT) process in the twisted PBI derivatives (0.9 ps), and the ISC takes 3.7 ns. Pulsed laser excited time-resolved electron paramagnetic resonance (TREPR) spectra indicate that the triplet-state wave function of the twisted PBIs is mainly confined on the PBI core, demonstrated by the zero-field-splitting D parameter. Accordingly, the twisted derivatives have higher T1 energy (ET1 = 1.48-1.56 eV) as compared to the native PBI chromophore (1.20 eV), which is an advantage for the application of the derivatives as triplet PSs. Theoretical computation of the Franck-Condon density of states, based on excited-state dynamics methods, shows that the efficient ISC in the twisted PBI derivatives is due to the increased spin-orbit coupling matrix elements for the S1-T1 and S1-T2 states [spin-orbit coupling matrix element (SOCME): 0.11-0.44 cm-1. SOCME is zero for native PBI], as well as the Herzberg-Teller vibronic coupling. For the planar benzoPBI, the moderate ISC is due to S1 → T2 transition (SOCME: 0.03 cm-1. The two states share a similar energy, ca. 2.5 eV).
- Mahmood, Zafar,Sukhanov, Andrey A.,Rehmat, Noreen,Hu, Mengyu,Elmali, Ayhan,Xiao, Yi,Zhao, Jianzhang,Karatay, Ahmet,Dick, Bernhard,Voronkova, Violeta K.
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- Heterologous perylene diimide arrays: Potential non-fullerene acceptors in organic solar cells
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A new family of perylene diimide (PDI) arrays, heterologous ones (di-PDI and tri-PDI), were designed and efficiently synthesized by Suzuki cross-coupling reactions using two heterologous PDI monomers with different positions of bay- and ortho-substitution, respectively. The compounds exhibit unique photophysical and electrochemical properties and were successfully applied in non-fullerene organic solar cells with a superior power conversion efficiency of 4.55% for tri-PDI.
- Wang, Helin,Chen, Lingcheng,Xiao, Yi
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- Robust Aqua Material: A Pressure-Resistant Self-Assembled Membrane for Water Purification
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“Aqua materials” that contain water as their major component and are as robust as conventional plastics are highly desirable. Yet, the ability of such systems to withstand harsh conditions, for example, high pressures typical of industrial applications has not been demonstrated. We show that a hydrogel-like membrane self-assembled from an aromatic amphiphile and colloidal Nafion is capable of purifying water from organic molecules, including pharmaceuticals, and heavy metals in a very wide range of concentrations. Remarkably, the membrane can sustain high pressures, retaining its function. The robustness and functionality of the water-based self-assembled array advances the idea that aqua materials can be very strong and suitable for demanding industrial applications.
- Cohen, Erez,Weissman, Haim,Shimoni, Eyal,Kaplan-Ashiri, Ifat,Werle, Kai,Wohlleben, Wendel,Rybtchinski, Boris
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- Near-IR phosphorescent ruthenium(II) and iridium(III) perylene bisimide metal complexes
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The phosphorescence emission of perylene bisimide derivatives has been rarely reported. Two novel ruthenium(II) and iridium(III) complexes of an azabenz-annulated perylene bisimide (ab-PBI), [Ru(bpy)2(ab-PBI)][PF6]2 1 and [CpIr-(ab-PBI)Cl]PF6 2 are now presented that both show NIR phosphorescence between 750-1000 nm in solution at room temperature. For an NIR emitter, the ruthenium complex 1 displays an unusually high quantum yield (Fp) of 11% with a lifetime (tp) of 4.2 ms, while iridium complex 2 exhibits Fp p =33 ms. 1 and 2 are the first PBI-metal complexes in which the spin-orbit coupling is strong enough to facilitate not only the Sn→Tn intersystem crossing of the PBI dye, but also the radiative T1→S0 transition, that is, phosphorescence.
- Schulze, Marcus,Steffen, Andreas,Würthner, Frank
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- Metal-free Annulation at the Ortho- and Bay-Positions of Perylene Bisimide Leading to Lateral π-Extension with Strong NIR Absorption
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A novel ortho/bay annulation reaction of perylene bisimide (PBI) has been explored in a single step synthetic procedure using perylene bisimide 1 and 1,8-Diazabicyclo[5.4.0]undec-7-ene (DBU) in the absence of any metal catalyst. The single crystal solid-s
- Regar, Ramprasad,Mishra, Ruchika,Mondal, Pradip Kumar,Sankar, Jeyaraman
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- O-Annulation to Polycyclic Aromatic Hydrocarbons: A Tale of Optoelectronic Properties from Five- To Seven-Membered Rings
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We take advantage of the Pummerer oxidative annulation reaction to extend PAHs through the formation of an intramolecular C-O bond with a suitable phenol substituent. Depending on the peripheral topology of the PAH precursor (e.g., pyrene, boron-dipyrromethene, or perylene diimide) five-, six-, and seven-membered O-containing rings could be obtained. The effect of the O-annulations on the optoelectronic properties were studied by various methods with the pyrano-annulated pyrene and BODIPY derivatives depicting quantitative emission quantum yields.
- Dordevi?, Luka,Milano, Domenico,Demitri, Nicola,Bonifazi, Davide
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- Porphyrin based push-pull conjugates as donors for solution-processed bulk heterojunction solar cells: A case of metal-dependent power conversion efficiency
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Solution-processed bulk-heterojunction organic solar cells have been achieved using unsymmetrical metalloporphyrin-PBI dyads as small molecular donors. Due to panchromatic absorption, a photon-to-current conversion efficiency of 6.18% was obtained for 3-Zn:PC71BM with a remarkable energy loss (Eloss) of 0.60 eV, which is in line with the best values recorded so far for porphyrin-based small-molecular donors.
- Mishra, Ruchika,Regar, Ramprasad,Singhal, Rahul,Panini, Piyush,Sharma, Ganesh D.,Sankar, Jeyaraman
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- A direct comparison of monomeric vs. dimeric and non-annulated vs. N-annulated perylene diimide electron acceptors for organic photovoltaics
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Herein we report on four perylene diimide (PDI) variants to study the effects that N-annulation and dimerization have on optoelectronic properties and organic solar cell device performance. The PDI compounds were synthesized following a scalable and efficient procedure and studied by cyclic voltammetry, solution and solid-state optical absorption spectroscopy, emission spectroscopy, and density functional theory analysis. The thin-film morphology was probed by optical and atomic force microscopy. Dimerization stabilized the frontier molecular orbital energy levels and reduced aggregation in the thin-films. N-Annulation resulted in a destabilization of the frontier molecular orbital energy levels in both the monomers and dimers and enabled the formation of smoother films with smaller domain sizes. Each PDI molecule was evaluated as a non-fullerene acceptor in bulk-heterojunction solar cells using the donor polymers PTB7-Th and PffBT4T-2OD. The dimers outperformed the monomers, while N-annulated PDIs led to devices with higher open-circuit voltages.
- Nazari, Maryam,Cieplechowicz, Edward,Welsh, Thomas A.,Welch, Gregory C.
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- Carbazole-perylenebisimide electron donor/acceptor dyads showing efficient spin orbit charge transfer intersystem crossing (SOCT-ISC) and photo-driven intermolecular electron transfer
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Perylenebisimide-carbazole (PBI-Cz) dyads were prepared to study charge-recombination (CR) induced intersystem crossing (ISC) in electron donor/acceptor dyads. The distance and the mutual orientation of the perylenebisimide (PBI) and carbazole (Cz) moieties were varied to study their effect on photophysical properties. Steady state and time-resolved optical spectroscopies show that electronic coupling between the electron donor and acceptor is negligible at the ground state. The fluorescence of the PBI moiety is strongly quenched in the dyads, and a larger separation between the donor and the acceptor results in less fluorescence quenching. The Gibbs free energy changes of the electron transfer and the energy level of the charge transfer state were studied using the electrochemical and optical spectra data. The singlet oxygen quantum yields (ΦΔ) are up to 72% for dyads with the shortest separation between the donor and the acceptor. Nanosecond transient absorption spectra confirmed the formation of the PBI-localized long lived triplet state (the lifetime is up to 190 μs). Notably non-orthogonal dyads show efficient spin orbit charge transfer (SOCT-ISC), which is different from the previously proposed orthogonal molecular structure for SOCT-ISC. Time-resolved electron paramagnetic resonance (TREPR) spectroscopy shows that all three dyads give the same electron spin polarization of eae/aea, and thus the radical pair ISC (RP ISC) mechanism is excluded, which is different from the previously reported PBI-phenothiazine analogues. Efficient and reversible transformation of dyads to their radical anion was observed in the presence of sacrificial electron donor triethanolamine in an inert atmosphere with photo-irradiation.
- Barbon, Antonio,Mahmood, Zafar,Rehmat, Noreen,Toffoletti, Antonio,Zhang, Xue,Zhao, Jianzhang
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- Null Exciton-Coupled Chromophoric Dimer Exhibits Symmetry-Breaking Charge Separation
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A comprehensive understanding of the structure-property relationships in multichromophoric architectures has pushed the limits for developing robust photosynthetic mimics and molecular photovoltaics. The elusive phenomenon of null exciton splitting has gathered immense attention in recent years owing to the occurrence in unique chromophoric architectures and consequent emergent properties. Herein, we unveil the hitherto unobserved null exciton coupling assisted highly efficient photoinduced symmetry-breaking charge separation (SB-CS) in a Greek cross (+)-oriented spiro-conjugated perylenediimide dimer (Sp-PDI2). Quantum chemical calculations have rationalized the infrequent manifestation of null exciton coupling behavior in Sp-PDI2. Negligible contribution of long-range Coulombic and short-range charge-transfer mediated coupling renders a monomer-like spectroscopic signature for Sp-PDI2 in toluene. The Greek cross (+)-arranged Sp-PDI2 possesses a selective hole-transfer coupling, facilitating the ultrafast dissociation of null excitons and evolution of the charge-separated state in polar solvents. Radical cationic and anionic spectroscopic signatures were characterized by employing femtosecond transient absorption spectroscopy. The substantial hole transfer electronic coupling and lower activation energy barrier of Sp-PDI2 accelerated the charge separation rate. The rate of charge recombination (CR) markedly decelerated due to falling into the inverted region of the Marcus parabola, where the driving force of CR is larger than the total reorganization energy for CR. Hence, the ratio of the rates for SB-CS over CR of Sp-PDI2 exhibited an unprecedently high value of 2647 in acetonitrile. The current study provides impeccable evidence for the role of selective charge filtering in governing efficient SB-CS and thereby novel insights towards the design of biomimics and advanced functional materials.
- Sebastian, Ebin,Hariharan, Mahesh
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- Fused perylenebisimide-carbazole: New ladder chromophores with enhanced third-order nonlinear optical activities
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A series of ladder chromophores featuring planar structures of fused perylenebisimide and carbazole have been efficiently synthesized via photocyclization under sun light. Compared to N,N′-bis(3-pentyl) perylenebisimide (PBI-1), they show remarkably enhanced nonlinear properties.
- Yang, Yang,Wang, Yaochuan,Xie, Yuanpeng,Xiong, Tao,Yuan, Zhongyi,Zhang, Youdi,Qian, Shixiong,Xiao, Yi
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- Phthalimide-based π-conjugated small molecules with tailored electronic energy levels for use as acceptors in organic solar cells
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The design, synthesis, and characterization of seven phthalimide-based organic π-conjugated small molecules are reported. The new materials are based on a phthalimide-thiophene-CORE-thiophene-phthalimide architecture. The CORE units utilized were phthalimide (M2), diketopyrrolopyrrole (M3), isoindigo (M4), naphthalene diimide (M5), perylene diimide (M6), and difluorobenzothiadiazole (M7); they were specifically selected to progressively increase the electron affinity of the resulting compound. A small molecule with no core (M1) was synthesized for comparison. Each material was synthesized through optimized direct heteroarylation cross-coupling procedures using bench top solvents in air. Combinations of UV-visible spectroscopy (UV-vis), cyclic voltammetry (CV), differential scanning calorimetry (DSC), ultraviolet photoelectron spectroscopy (UPS) and density functional theory (DFT) were used to characterize each material. The use of various core acceptor building blocks with differing electron affinities resulted in the series M1-M7 having a range of energetically deep LUMO levels and a range of HOMO-LUMO gap energies. Meanwhile, the melting and crystallization temperatures of the molecules M1-M7 were also found to vary according to the change in central acceptor unit. Compounds M1-M7 were employed as acceptors in combination with either the polymeric donor P3HT or small molecule donor DTS(FBTTh2)2 to understand how the LUMO levels of each acceptor influences the open circuit voltage (Voc). It was found that, in general, Voc was only weakly related to the offset between the HOMO energy level of the donor and LUMO level of the acceptor used, with a Voc of up to 1.2 V being achieved for M1.
- Hendsbee, Arthur D.,McAfee, Seth M.,Sun, Jon-Paul,McCormick, Theresa M.,Hill, Ian G.,Welch, Gregory C.
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- Synthesis, photophysical and electrochemical properties of bay-axial perylene diimide-subphthalocyanine dyads
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Two novel perylene diimide-subphthalocyanine dyads in which the two macrocycles are linked together by a B-O bond have been synthesized. The electronic communication between the two chromophores was investigated by photophysical and electrochemical studie
- Kasi Viswanath, Lakshmi C.,Shirtcliff, Laura D.,Krishnan,Handa, Nisha V.,Darrell Berlin
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- Synthesis, luminescence, and excited-state absorption properties of disubstituted perylene diimide derivatives modified at bay region
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Three A–π–A or D–π–D perylene diimide (PDI) derivatives with varied groups on π-conjugate were synthesized and characterized. The photophysical properties of these compounds were systematically studied by spectral experiments and density functional theory
- Cheng, Qian,Chen, Zhiyuan,Zhang, Qing,Zhu, Senqiang,Liu, Rui,Zhu, Hongjun
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p. 247 - 254
(2021/12/01)
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- Perylene diimide derivative as well as preparation method and application thereof
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The invention discloses a perylene diimide derivative and a preparation method and application thereof, and belongs to the field of photoelectric materials. A perylene diimide derivative having bay-position introduction of ortho-biphenyl. The meta bipheny
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Paragraph 0123-0126
(2021/09/08)
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- Perylene diimide shoulder tetra-substituted derivative as well as preparation method and application thereof
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The invention discloses a perylene diimide shoulder four-substituted derivative and a preparation method and application thereof, and constructs a conjugated molecule system covalently linked with a plurality of electron donors and a single electron acceptor, namely a perylene diimide shoulder tetrasubstituted derivative. Electron coupling between electrons to the receptor results in a broadening of the light absorption range of the compound and, at the same time, the charge separated state formed under the light excitation conditions can be returned to the ground state by intersystem blowby or in a non-radiative transition form. This is why the derivative has excellent active oxygen generation efficiency and photo-thermal conversion efficiency. The derivative has high active oxygen production rate. The photo-thermal conversion effect is obvious, is a photosensitizer and an organic small molecule photothermal material with excellent performance, and is expected to be applied to the field of solar water purification engineering, clinical photothermal/photodynamic therapy of tumors. A new idea is provided for designing a photosensitizer and a photo-thermal agent with excellent performance.
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Paragraph 0059; 0061; 0062; 0063; 0064
(2021/08/14)
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- Visible-light photocatalytic aerobic oxidation of sulfides to sulfoxides with a perylene diimide photocatalyst
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Photosensitized oxygenation has been recognised as a modern method of incorporating oxygen into a substrate, as it offers environmentally benign alternatives to several conventional synthetic procedures. A metal-free aerobic selective sulfoxidation photos
- Gao, Yueying,Xu, Huan,Zhang, Shiwei,Zhang, Yan,Tang, Chunlei,Fan, Weizheng
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supporting information
p. 7144 - 7149
(2019/08/07)
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- Modulation of the power conversion efficiency of organic solar cells via architectural variation of a promising non-fullerene acceptor
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Thiophene-containing molecular materials are recognised as efficient substrates in organic photovoltaics. Herein, we have demonstrated the effect of substitution patterns of thiophenes on the electron accepting ability of perylene bisimide derivatives, which in turn dictates the photovoltaic performance. The thiophene units were integrated through α- or β-positions on the 1- or 1,7-bay positions of perylene-bisimide through alkyne spacers in order to modulate the electronic properties of PBI. The target molecules are structurally robust as per electrochemical studies and exhibited broad absorption in the visible region. Better light harvesting ability and favourable LUMO energy levels render these dyads and triads suitable as electron acceptors in organic solar cells. Bulk heterojunction solar cells were constructed from thienyl-PBI (1-4) as acceptors and a polymer P as a donor. α-Linked 1 and 3 showed a PCE of 5.72% and 6.94% with a remarkable energy loss of 0.55 eV and 0.58 eV, respectively whereas, β-linked 2 and 4 showed an overall PCE of 4.93% and 6.06% with an energy loss of 0.52 eV and 0.54 eV, respectively.
- Mishra, Ruchika,Regar, Ramprasad,Singh, Varun,Panini, Piyush,Singhal, Rahul,Keshtov,Sharma, Ganesh D.,Sankar, Jeyaraman
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supporting information
p. 574 - 582
(2018/01/12)
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- NITROGEN ANNULATED PERYLENE DIIMIDES FOR USE AS ELECTRON TRANSPORT MATERIALS IN ORGANIC ELECTRONIC DEVICES
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PDI derivatives useful as opto-electronically active materials or for the synthesis of such materials. Certain compounds herein function as efficient electron acceptors and are useful as electron active components of electronic devices.
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Paragraph 0137; 0138
(2018/01/11)
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- PERYLENE DIIMIDE BASED MEMBRANE AND METHODS OF USE THEREOF
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This invention is directed to filtration system, filtration apparatus and methods of use thereof, wherein the filtration system comprises a solid support, perylene diimide based membrane layer and a polymer, specifically a Nafion polymer. The system and apparatus of this invention enables filtration of solutes such as: dyes, salts, heavy metal ions, pharmaceuticals and small organic molecules.
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Paragraph 00158; 00159
(2017/02/09)
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- A substituted bay position gold[...] imide derivatives (by machine translation)
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A substituted bay position gold[...] imide derivatives, its chemical formula is R 2-PDI-R 1, the structural formula , In the formula: derivatives in PDI-a R 1 to PPh 3, R 2 to H; derivative compound in PDI-b R 1 to PPh 3, R 2 to Au-PPh 3; in PDI-b the derivation gathers the thing R1 to C ≡ N-Ph, R 2 to H. Substituted position goldstates the bay[...] the preparation process of imide derivative, the steps are as follows : (1) synthesis of diamide derivatives perylen ; (2) synthesis of gold-containing derivatives. The advantage of this invention is: the method of preparing substituted bay position gold[...] imide derivatives, fluorescent obviously enhance and stable properties, good heat conducting properties, in aviation and aerospace, photoelectric. Many machinery and the like, and have a wide range of application prospect. (by machine translation)
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Paragraph 0027; 0048
(2017/02/09)
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- Synthesis, photophysical and electrochemical properties of bay-axial perylene diimide-subphthalocyanine dyads
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Two novel perylene diimide-subphthalocyanine dyads in which the two macrocycles are linked together by a B-O bond have been synthesized. The electronic communication between the two chromophores was investigated by photophysical and electrochemical studie
- Kasi Viswanath, Lakshmi C.,Shirtcliff, Laura D.,Krishnan,Handa, Nisha V.,Darrell Berlin
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p. 4199 - 4202
(2015/02/18)
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- THIONATED AROMATIC BISIMIDES AS ORGANIC SEMICONDUCTORS AND DEVICES INCORPORATING THEM
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Disclosed are thionated fused-ring (aromatic) imides and diimides that can exhibit desirable electronic properties and can possess processing advantages including solution- processability and/or good stability at ambient conditions.
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Page/Page column 52
(2011/07/30)
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- Syntheses and properties of 1,6 and 1,7 perylene diimides and tetracarboxylic dianhydrides
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Via Sonogashira cross-coupling with different alkynes, 1,6 and 1,7 perylene diimides (PDIs) and perylene tetracarboxylic dianhydrides (PTCDs) were synthesized from the corresponding regioisomeric mixture of 1,6/1,7-dibromo precursors. Both bulky triphenyl
- Handa, Nisha V.,Mendoza, Kayla D.,Shirtcliff, Laura D.
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scheme or table
p. 4724 - 4727
(2011/10/13)
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- A novel 2,7-linked carbazole based "double cable" polymer with pendant perylene diimide functional groups: Preparation, spectroscopy and photovoltaic properties
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The preparation and chemical analysis of a 'double-cable' conjugated polymer comprising a backbone of alternating 2,7-linked carbazole repeat units with covalently attached perylene diimide (PDI) substituents and dithienyl repeat units is presented. The b
- Mohamad, David K.,Fischereder, Achim,Yi, Hunan,Cadby, Ashley J.,Lidzey, David G.,Iraqi, Ahmed
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supporting information; experimental part
p. 851 - 862
(2011/09/15)
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- Self-assembly of semifluorinated minidendrons attached to electron-acceptor groups into pyramidal columns
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The synthesis and self-assembly of twelve semifluorinated first-generation dendrons or minidendrons attached to electron-acceptor (n-type) groups generated from various combinations of eight acceptors and three dendrons arc reported. Dendrons attached to small electron-acceptor molecules mediate their self-assembly into π-stacks located in the center of a supramolecular helical pyramidal column with the long axis of the acceptor perpendicular to the long axis of the column. Dendrons attached to large electron-acceptor molecules, such as perylene bisimide, mediate the assembly of their acceptors in an unprecedented arrangement of π-stacks that have the long axis of the acceptors parallel to the long axis of the supramolecular pyramidal column. All supra_molecular columns self-organize into various periodic columnar arrays that exhibit liquid-crystalline phases, crystalline phases, or a liquid-crystalline phase with enhanced intracolumnar order. The present study demonstrates the simplicity and the versatility of the concept of assembly of π-type electroactive groups mediated by semifluorinated dendrons and assesses the scope and limitations of this supramolecular strategy.
- Percec, Virgil,Aqad, Emad,Peterca, Mihai,Imam, Mohammad R.,Glodde, Martin,Bera, Tusha K.,Miura, Yoshiko,Balagurusamy, Venkatachalapathy S. K.,Ewbank, Paul C.,Wuerthner, Frank,Heiney, Paul A.
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p. 3330 - 3345
(2008/02/07)
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- Very Soluble and Photostable Perylene Fluorescent Dyes
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The synthesis of perylene dyes 2 with two terminal alkyl groups is described.Long-chain alkyl groups do not increase, but diminish solubility.Cycloalkyl substituents give a minimum of solubility with medium sized rings and a maximum with the cyclotetradecyl derivative (2p).Very high solubility in organic solvents is attained by substitution with secondary alkyl residues having two long chains.One of them, the dye with the 1-hexylheptyl substituent (2v), exhibits a solubility of more than 100g/l in most solvents, a fluorescent quantum yield of about 100 percent, and a very high photostability, thus making it suitable for special applications.
- Demming, Stefan,Langhals, Heinz
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p. 225 - 230
(2007/10/02)
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