191997-95-2Relevant articles and documents
Selective bromination of perylene diimides under mild conditions
Rajasingh, Paramasivan,Cohen, Revital,Shirman, Elijah,Shimon, Linda J. W.,Rybtchinski, Boris
, p. 5973 - 5979 (2007)
(Chemical Equation Presented) A novel method for the bromination of perylene diimides, PDI (1), under mild conditions is reported. Variation of the reaction conditions allows mono- and dibromination of PDIs to afford 2 and 3 (these can be separated throug
Preparation and characterization of regioisomerically pure 1,7-disubstituted perylene bisimide dyes
Wuerthner, Frank,Stepanenko, Vladimir,Chen, Zhijian,Saha-Moeller, Chantu R.,Kocher, Nikolaus,Stalke, Dietmar
, p. 7933 - 7939 (2004)
A detailed study on bromination and subsequent imidization of perylene bisanhydride with cyclohexylamine is reported. The present results reveal that previously reported 1,7-difunctionalized perylene bisimides are presumably contaminated with the respecti
Modulating optical and electrochemical properties of perylene dyes by twisting aromatic π-system structures
Wang, Ying,Zhang, Qi,Gong, Junbo,Zhang, Xin
, (2021/03/04)
Three highly fluorescent perylene bisimide dyes were synthesized, where aromatic π-system structures are twisted to different degree by steric hindrance of two or four substitution groups at bay position. Light-emitting colours of these dye solutions can be modulated from green, yellow to red, and their fluorescence quantum yields increase up to approximate 100% with increasing the π-system twisting, which can be considered for new class of wavelength-tunable dye lasers. π-Twisted dyes are more sensitive to microenvironment changes. Thus, they are better fluorescence probe and sensory materials than planar dyes. Electrochemical cyclic voltammetry measurements revealed that these dyes are suitable for n-type optoelectrical devices and materials. These dye solids display near infra-red emission at 600–850 nm. Owing to strong π-π stacking interaction, planar dye solid loses its outstanding optical properties compared to its solution. In contrast, π-twisted dye solids retain their excellent optical properties including narrow emission bands and relatively high fluorescence quantum yields due to the suppression of π-π stacking interaction. Exceptional fluorescence polarization phenomena were observed for these π-twisted dye solids. These optical results revealed that π-twisted perylene bisimide dyes are more excellent optical materials than planar dyes.
Tuning the aggregation behaviour of BN-coronene diimides with imide substituents and their performance in devices (OLEDs and OFETs)
Geffroy, Bernard,Hissler, Muriel,Hoffmann, Jonas,Jaques, Emmanuel,Staubitz, Anne
supporting information, p. 14720 - 14729 (2021/11/09)
Compared to perylene diimides (PDIs), coronene diimides (CDIs), which can be viewed as a lateral core extension, show undesired effects for optoelectronic devices such as the decrease of the absorption and a hypsochromic shift. Here, we demonstrate that, if the core is extended with two BN units as opposed to two CC units, the opposite is true: large bathochromic shifts can be achieved, together with higher molar extinction coefficients and beneficial luminescence properties,e.g.small Stokes shifts and high quantum yields (Φlum> 94%). These effects can be explained by the influence of the BN-unit on the frontier molecular orbitals of theBNCDIs. Different substitution motifs at the imide position, cyclohexyl and 2,6-diisopropylphenyl, although they had no influence on the optical properties on a single molecule level, influenced the aggregation substantially so that the optical properties in the solid state and the performance in organic devices (OLEDs and OFETs) differed considerably. In combination with host matrices, devices with EQEs of up to 1.5% and white light emission (0.317; 0.346) were obtained. The developed synthetic route starting from a regioisomeric pure 1,7-substituted PDI leads toBNCDIs in good yields, which makes this class of compounds very promising.
BN-Substituted coronene diimide donor-acceptor-donor triads: photophysical, (spectro)-electrochemical studies and Lewis behavior
Hissler, Muriel,Hoffmann, Jonas,Jacquemin, Denis,Staubitz, Anne
supporting information, p. 13926 - 13934 (2021/10/20)
Boron/nitrogen substituted polyaromatic hydrocarbons (PAHs) are unique materials, with similar molecular structures to their carbon/carbon analogs, but different electronic properties. We report how these may be tuned by substitution at the B and/or N ato
Fluorescent probe PDI-CMA for continuously detecting Cu and dopamine as well as preparation method and application thereof
-
Page/Page column 0029; 0032; 0035, (2021/07/17)
The invention belongs to the field of fluorescent probes, and relates to preparation and application of a perylene bisimide fluorescent probe, in particular to a fluorescent probe for continuous detection of Cu and dopamine as well as a preparatio
Desymmetrization of Perylenediimide Bay Regions Using Selective Suzuki–Miyaura Reactions from Dinitro Substituted Derivatives
Hruzd, Mariia,Rocard, Lou,Goujon, Antoine,Allain, Magali,Cauchy, Thomas,Hudhomme, Piétrick
supporting information, p. 15881 - 15891 (2020/10/12)
Bay decoration of perylenediimide (PDI) is an attractive approach for tuning the optoelectronic properties of the dye as well as breaking backbone planarity, which provides the possibility of preventing the undesired formation of aggregates. This is usual
Controllable Monobromination of Perylene Ring System: Synthesis of Bay-Functionalized Perylene Dyes
Takahashi, Masaki,Asaba, Kyohei,Lua, Trinh Thi,Inuzuka, Toshiyasu,Uemura, Naohiro,Sakamoto, Masami,Sengoku, Tetsuya,Yoda, Hidemi
supporting information, p. 624 - 631 (2018/01/27)
Practical synthesis of bay-monofunctionalized perylene dyes has been developed based on controllable NBS bromination of tetrabenzyl perylene-3,4,9,10-tetracarboxylate. The ability to perform the convenient and high-yielding synthesis highlights the potential utility of our multifunctional approach to access a diverse range of new perylene systems.
The Photostability of Two Optical Materials Based on Perylene Diimide Substituted by Different Aromatic Groups at the Bay Area
He, Junjie,Li, Song,Zeng, Heping
, p. 2800 - 2807 (2017/09/26)
The perylene diimide substituented by thiophene rings at bay area shows photoactivity and can be used as a photo sensor, but another one substituented by mestylene groups is photostable. The single crystal of 1,7-mesitylene perylene diimide was obtained. X-ray diffraction data of the crystal revealed that the plane of the perylene core was hardly twisted by introduction of mesitylene groups. These mestylene groups are like clips maintaining the planarity of the perylene core. Density functional theory calculation was applied to study the difference of photophysical and photochemical properties. The discovery is valuable for design guidance of perylene diimides.
Perylene diimide organic third-order nonlinear optical material, and preparation and application of perylene diimide organic third-order nonlinear optical material
-
Paragraph 0036, (2017/08/23)
The invention relates to a perylene diimide organic third-order nonlinear optical material. 3,4,9,10-perylenetetracarboxylic diimide serves as a core group; cyclohexane and benzanthrone or triphenylamine serve as substituent groups; cyclohexane is connected with an imide nitrogen atom of the core group; and benzanthrone or triphenylamine is connected with a bay of the core group to form a whole. A preparation method comprises the steps: (1) adding a perylene diimide derivative, a benzanthrone derivative or a triphenylamine derivative with the imide nitrogen atom connected with cyclohexane, and potassium carbonate into a solvent for dissolution, (2) after supplying nitrogen for 1-30 min, adding a tetrakispalladium catalyst, heating to 80-100 DEG C at a speed of 500-1200 r/min for reaction for 3-24h , (3) carrying out extraction, knockout and dryness for many times by using dichloromethane and distilled water, and (4) separating and purifying an obtained crude product. The perylene diimide organic third-order nonlinear optical material has a large nonlinear absorption coefficient and a two-photon absorption cross-section value and is applied to a third-order nonlinear optical material aspect.
