209111-67-1Relevant academic research and scientific papers
Tuning orbital energetics in arylene diimide semiconductors. Materials design for ambient stability of n-type charge transport
Jones, Brooks A.,Facchetti, Antonio,Wasielewski, Michael R.,Marks, Tobin J.
, p. 15259 - 15278 (2007)
Structural and electronic criteria for ambient stability in n-type organic materials for organic field-effect transistors (OFETs) are investigated by systematically varying LUMO energetics and molecular substituents of arylene diimide-based materials. Six OFETs on n+-Si/SiO2 substrates exhibit OFET response parameters as follows: N,N′-bis(n-octyl) perylene-3,4:9, 10-bis(dicarboximide) (PDI-8): μ = 0.32 cm2 V -1 s-1 Vth = 55 V, Ion/I off = 105; N,N′-bis(n-octyl)-1,7- and N,N′-bis(n-octyl)-1,6-dibromoperylene-3,4:9, 10-bis-(dicarboximide) (PDI-8Br2): μ = 3×10-5 cm2 V -1 s-1, Vth = 62 V, Ion/Ioff = 103; N,N′-bis(n-octyl)-1,6,7,12-tetrachloroperylene-3,4:9,10- bis(dicarboximide) (PDI-8Cl4): μ = 4 × 10-3 cm2 V-1 s_1, Vth = 37 V, I on/Ioff = 104; N,N′-bis(n-octyl)-2- cyanonaphthalene-1,4,5,8-bis(dicarboximide) (NDI-8CN): μ = 4.7 × 10-3 cm2 V-1 s-1, Vth = 28, Ion/Ioff = 105; N,N′-bis(n-octyl)-1, 7- and N,N′-bis(n-octyl)-1,6-dicyanoperylene-3,4:9,10-bis-(dicarboximide) (PDI-8CN2): μ = 0.13 cm2 V-1 s 1, Vth = -14 V, Ion/Ioff = 103; and N,N′-bis(n-octyl)-2,6-dicyanonaphthalene-1,4,5,8-bis(dicarboximide) (NDI-8CN2): μ = 0.15 cm2 V-1 s_1, Vth = -37 V, Ion/Ioff = 102. Analysis of the molecular geometries and energetics in these materials reveals a correlation between electron mobility and substituent-induced arylene core distortion, while Vth and I0ff are generally affected by LUMO energetics. Our findings also indicate that resistance to ambient charge carrier trapping observed in films of N-(n-octyl)arylene diimides occurs at a molecular reduction potential more positive than ～ -0.1 V (vs SCE). OFET threshold voltage shifts between vacuum and ambient atmosphere operation suggest that, at Ered1 13 cm-2, while, for semiconductors with Ered1 > -0.1 V, the trap density increase is negligible. OFETs fabricated with the present n-type materials having E red1 > -0.1 V operate at conventional gate biases with minimal hysteresis in air. This reduction potential corresponds to an overpotential for the reaction of the charge carriers with O2 of ～0.6 V. N,N′-1H,1H-Perfluorobutyl derivatives of the perylene-based semiconductors were also synthesized and used to fabricate OFETs, resulting in air-stable devices for all fluorocarbon-substituted materials, despite generally having Ered1 2 barrier mechanism. OFET cycling measurements in air for dicyanated vs fluorinated materials demonstrate that energetic stabilization of the charge carriers results in greater device longevity in comparison to the OFET degradation observed in air-stable semiconductors with fluorocarbon barriers.
Complementary Photocatalytic Toolbox: Control of Intramolecular endo-versus exo-trig Cyclizations of α-Phenyl Olefins to Oxaheterocyclic Products
Belov, Arina,Steuernagel, Desirée,Wagenknecht, Hans-Achim,Weick, Fabian
supporting information, (2022/03/03)
The regioselectivity of the intramolecular cyclization of bifunctional α-phenyl alkenes can be controlled simply by the choice of the organic chromophore as the photocatalyst. The central photoredox catalytic reaction in both cases is a nucleophilic addition of the hydroxyl function to the olefin function of the substrates. N,N-(4-Diisobutylaminophenyl) phenothiazine catalyzes exo-trig cyclizations, whereas 1,7-dicyanoperylene-3,4,9,10-tetracarboxylic acid bisimides catalyze endo-trig additions to products with anti-Markovnikov regioselectivity. We preliminarily report the photoredox catalytic conversions of 11 representative substrates into 20 oxaheterocycles in order to demonstrate the similarity, but also the complementarity, of these two variants in this photoredox catalytic toolbox.
NARROW ABSORPTION POLYMER NANOPARTICLES AND RELATED METHODS
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Page/Page column 184, (2020/04/25)
Polymers, monomers, narrow-band absorbing polymers, narrow-band absorbing monomers, absorbing units, polymer dots, and related methods are provided. Bright, luminescent polymer nanoparticles with narrow-band absorptions are provided. Methods for synthesizing absorbing monomers, methods for synthesizing the polymers, preparation methods for forming the polymer nanoparticles, and applications for using the polymer nanoparticles are also provided.
The effect of imide substituents on the optical properties of perylene diimide derivatives
Kong, Fan,Lin, Mengqi,Qiu, Teng
, p. 1209 - 1216 (2018/09/12)
As one of the most important organic semiconductors, perylene diimide derivatives (PDIs) have been widely applied in optoelectronics. Two kinds of soluble PDIs with different imide substituents have been synthesized and their optical properties have been investigated. The photoluminescence (PL) intensity of the PDI with amino phenyl imide substituents (NH2-PDI) is much lower than that of the PDI with octyl imide substituents (O-PDI). It can be found that the Stokes shift of O-PDI is positive, whereas, the Stokes shift of NH2-PDI is negative. The emission intensity of the 0–0 electron transition relative to that of the 1–0 electron transition (I0–0/I1–0) in the PL spectrum of O-PDI is decreased, but the value of I0–0/I1–0 in the PL spectra of NH2-PDI is increased as the dielectric constant of the solvent increases. The large overlap between the absorption and PL spectra plays an important role to result in the low PL intensity of NH2-PDI. The PL decay data show that a non-radiative process, photoinduced electron transfer, also contributes to the low PL intensity of NH2-PDI. The results can help researchers to understand the effect of the imide substituents on the optical properties of PDIs.
Synthesis, mesomorphic and photophysical properties of novel triads and pentads of perylene liquid crystals with cholesterol units at the bay-position
Zhu, Mingguang,Guo, Hongyu,Yang, Fafu,Wang, Zusheng
, p. 4320 - 4328 (2017/01/29)
Series of triads and pentads of perylene derivatives with two cholesterol units at the bay-position or four cholesterol units on both bay-position and imide position were designed and synthesized in yields of 55-65%. The influence of the different number and position of cholesterol substituents on mesomorphic properties and photophysical properties was studied. The results suggested that, in comparison with similar perylene derivatives with alkyl units at the imide position, the perylene liquid crystals with alkyl units at the bay-positions not only maintained excellent mesomorphic properties but also enhanced the fluorescence greatly. More cholesterol units resulted in a lower mesophase temperature, wider phase transfer temperature range, and higher fluorescence. A long spacer between perylene and cholesterol units led to more excellent mesomorphic properties and higher fluorescence.
Highly Segregated Lamello-Columnar Mesophase Organizations and Fast Charge Carrier Mobility in New Discotic Donor-Acceptor Triads
Zhao, Ke-Qing,An, Ling-Ling,Zhang, Xiao-Bo,Yu, Wen-Hao,Hu, Ping,Wang, Bi-Qin,Xu, Jing,Zeng, Qing-Dao,Monobe, Hirosato,Shimizu, Yo,Heinrich, Beno?t,Donnio, Bertrand
supporting information, p. 10379 - 10390 (2015/07/07)
Four new donor-acceptor triads (D-A-D) based on discotic and arylene mesogens have been synthesized by using Sonogashira coupling and cyclization reactions. This family of triads consists of two side-on pending triphenylene mesogens, acting as the electron-donating groups (D), laterally connected through short lipophilic spacers to a central perylenediimide (PI), benzo[ghi]perylenediimide (BI), or coronenediimide (CI) molecular unit, respectively, playing the role of the electron acceptor (A). All D-A-D triads self-organize to form a lamello-columnar oblique mesophase, with a highly segregated donor-acceptor (D-A) heterojunction organization, consequent to efficient molecular self-sorting. The structure consists in the regular alternation of two disrupted rows of triphenylene columns and a continuous row of diimine species. High-resolution STM images demonstrate that PI-TP2 forms stable 2D self-assembly nanostructures with some various degrees of regularity, whereas the other triads do not self-organize into ordered architectures. The electron-transport mobility of CI-TP2, measured by time-of-flight at 200C in the mesophase, is one order of magnitude higher than the hole mobility. By means of this specific molecular designing idea, we realized and demonstrated for the first time the so-called p-n heterojunction at the molecular level in which the electron-rich triphenylene columns act as the hole transient pathways, and the coronenediimide stacks form the electron-transport channels.
Diaryl-substituted perylene bis(imides): Synthesis, separation, characterization and comparison of electrochemical and optical properties of 1,7-and 1,6-regioisomer
Dey, Somnath,Efimov, Alexander,Lemmetyinen, Helge
scheme or table, p. 2367 - 2374 (2012/05/20)
A series of diaryl-substituted perylene bis(imides) (PBIs) containing electron-donating and-withdrawing aryl groups in the bay region (1-, 6-, 7-and/or 12-positions of the perylene core) were synthesized by Suzuki coupling reaction. The corresponding regioisomers, namely, 1,7-and 1,6-regioisomer, were separated from the mixture by conventional column chromatography without any need of recrystallization. All the individual regioisomers were fully characterized by 1H NMR and HRMS spectroscopy. The compounds were studied by optical spectroscopy and electrochemical techniques. The optical and electrochemical properties of 1,7-regioisomer are slightly different from the 1,6-regioisomer of the respective diaryl-PBI. Significant redshift and broadening of the absorption and emission maxima were observed in all synthesized PBIs depending upon the electronic nature of the attached aryl group. This is very first time such large series of 1,6- diarylperylenetetracarboxydiimides with their corresponding 1,7-regioisomers were synthesized, separated, characterized and studied in detail. 1,7-and 1,6-rsegioisomers of a series of diarylperylenetetracarboxydiimide derivatives were synthesized, separated, and electrochemical and spectroscopic studies have been done in detail. The regioisomers are chromatographically separable and fully characterized by 1H NMR spectroscopy.
Regioisomers of perylenediimide: Synthesis, photophysical, and electrochemical properties
Keerthi, Ashok,Valiyaveettil, Suresh
experimental part, p. 4603 - 4614 (2012/07/02)
A series of conjugation extended donor-acceptor 1,6- and 1,7-regiomers of perylenediimide were synthesized, separated, and characterized. The photophysical, electrochemical, and thermal properties of these compounds were investigated and compared. The absorption spectra of 1,6-substituted PDI showed blue shift as compared to its 1,7-substituted PDI. At the same time, the emission spectrum showed no significant differences among the regiomers. Both 1,6- and 1,7-regiomers were thermally stable up to 450 ?°C and showed different melting and crystallization transitions. The electrochemical studies did not show significant differences in oxidation and redox potentials owing to similar HOMO/LUMO gap of 1,6- and 1,7-regiomers, which is also supported by theoretical calculations. Comparison of properties of a series of 1,6- or 1,7-substituted PDIs showed significant differences. Such regiomerically pure compounds can offer certain advantages in applications, which are currently being investigated. ? 2012 American Chemical Society.
N-TYPE ORGANIC SEMICONDUCTORS INCLUDING AT LEAST TWO 2-DICYANOMETHYLENE-3-CYANO-2,5-DIHYDROFURAN GROUPS
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Page/Page column 13-14, (2012/05/20)
The invention relates to a method for manufacturing transistors. Said method involves using a molecule including at least two 2-dicyanomethylene-3-cyano-2,5-dihydrofuran groups. The invention can be implemented in particular in the field of electronics.
Bay region borylation of perylene bisimides
Dey, Somnath,Efimov, Alexander,Lemmetyinen, Helge
scheme or table, p. 5955 - 5958 (2011/12/14)
Novel bispinacolborane-N,N′-bis(octyl)-3,4,9,10- perylenetetracarboxylic acid bisimide (PBI) was synthesized in high yield. The title compound is a key intermediate in the preparation of PBI aryl derivatives through Suzuki cross-coupling by using a large variety of easily accessible aryl halides. The benign effect of a nonpolar solvent, mild base, and high reaction temperature on the borylation reaction was studied, and the reaction conditions were optimized accordingly. To demonstrate the potential and flexibility of the proposed building block, two corresponding bisarylperylene bisimides were prepared in high yields. For the first time, an efficient and straightforward method was developed for thesynthesis of bis-pinacolborane-N,N′-bis(octyl) -3,4,9,10-perylene tetracarboxylic bisimide derivatives by using a commercially available Pd catalyst. Two Suzuki cross-coupling reactions of novel bispinacolborane perylene derivative are also reported.
