110590-81-3Relevant articles and documents
Alkyl- and aryl-substituted benzo[ghi]perylenetriimides: Synthesis, characterization and comparison of electrochemical and spectroscopic properties
Viswanath, Lakshmi C. Kasi,Bernhardt, Jeremy,Kumar Gnanasekaran, Krishna,Want, Colton,Frank, Joshua,Faulkner, Jantzen,Krishnan, Sadagopan
, p. 453 - 458 (2016)
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
Self-Assembled Perylene Bisimide-Cored Trigonal Prism as an Electron-Deficient Host for C60and C70Driven by "like Dissolves Like"
Chang, Xingmao,Fang, Yu,Lin, Simin,Liu, Kaiqiang,Shang, Congdi,Stang, Peter J.,Wang, Gang,Wang, Zhaolong
, p. 15950 - 15960 (2020)
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.
Intersystem Crossing and Triplet-State Property of Anthryl- And Carbazole-[1,12]fused Perylenebisimide Derivatives with a Twisted π-Conjugation Framework
Mahmood, Zafar,Sukhanov, Andrey A.,Rehmat, Noreen,Hu, Mengyu,Elmali, Ayhan,Xiao, Yi,Zhao, Jianzhang,Karatay, Ahmet,Dick, Bernhard,Voronkova, Violeta K.
, p. 9317 - 9332 (2021)
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).
Robust Aqua Material: A Pressure-Resistant Self-Assembled Membrane for Water Purification
Cohen, Erez,Weissman, Haim,Shimoni, Eyal,Kaplan-Ashiri, Ifat,Werle, Kai,Wohlleben, Wendel,Rybtchinski, Boris
, p. 2203 - 2207 (2017)
“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.
Metal-free Annulation at the Ortho- and Bay-Positions of Perylene Bisimide Leading to Lateral π-Extension with Strong NIR Absorption
Regar, Ramprasad,Mishra, Ruchika,Mondal, Pradip Kumar,Sankar, Jeyaraman
, p. 9547 - 9552 (2018)
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
Porphyrin based push-pull conjugates as donors for solution-processed bulk heterojunction solar cells: A case of metal-dependent power conversion efficiency
Mishra, Ruchika,Regar, Ramprasad,Singhal, Rahul,Panini, Piyush,Sharma, Ganesh D.,Sankar, Jeyaraman
, p. 15529 - 15533 (2017)
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.
Carbazole-perylenebisimide electron donor/acceptor dyads showing efficient spin orbit charge transfer intersystem crossing (SOCT-ISC) and photo-driven intermolecular electron transfer
Barbon, Antonio,Mahmood, Zafar,Rehmat, Noreen,Toffoletti, Antonio,Zhang, Xue,Zhao, Jianzhang
, p. 4701 - 4712 (2020)
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.
Fused perylenebisimide-carbazole: New ladder chromophores with enhanced third-order nonlinear optical activities
Yang, Yang,Wang, Yaochuan,Xie, Yuanpeng,Xiong, Tao,Yuan, Zhongyi,Zhang, Youdi,Qian, Shixiong,Xiao, Yi
, p. 10749 - 10751 (2011)
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.
Synthesis, photophysical and electrochemical properties of bay-axial perylene diimide-subphthalocyanine dyads
Kasi Viswanath, Lakshmi C.,Shirtcliff, Laura D.,Krishnan,Handa, Nisha V.,Darrell Berlin
, p. 4199 - 4202 (2014)
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
Perylene diimide derivative as well as preparation method and application thereof
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Paragraph 0123-0126, (2021/09/08)
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
