- Swallow-tail substituted liquid crystalline perylene bisimides: Synthesis and thermotropic properties
-
Tailor-made synthesis and structure-property relationship of several swallow-tail N-substituted perylene bisimide (PBI) dyes are presented. PBI derivatives were synthesized by two distinct synthetic approaches, the details being evaluated herein. All the PBIs carry either alkyl swallow-tail or oligoethylenglycolether (OEG) swallow-tail moieties as N-substituents, and many of them are unsymmetrically substituted. We avoided substitution at bay positions of the perylene core to maintain the planarity and strong π-π interactions, which favor intermolecular order and charge carrier transport. The thermotropic behavior, which is strongly influenced by the nature of the substituents was investigated using differential scanning calorimetry (DSC), polarization optical microscopy (POM), and X-ray diffraction measurements (XRD). The introduction of OEG swallow-tail units facilitates thermotropic liquid crystalline behavior in most cases and the unsymmetrical substitution allowed the tuning of the mesophase-width. The mesophases exhibit characteristic columnar hexagonal (Colh) packing arising from π-π interactions between cofacially orientated perylene molecules. Thus, the inherent tendency of PBI molecules for crystallization could be effectively suppressed by incorporating flexible OEG swallow-tail units only at imide positions. This molecular design was crucial to obtain liquid crystallinity and intracolumnar long-range order. The substituents did not influence the electronic energy levels such as HOMO and LUMO.
- Wicklein, Andre,Lang, Andreas,Muth, Mathis,Thelakkat, Mukundan
-
-
Read Online
- Chemical engineering of donor-acceptor liquid crystalline dyads and triads for the controlled nanostructuration of organic semiconductors
-
Multi-segregated columnar structures provide a geometrically ideal scheme for ambipolar organic semiconductors, but are not easy to design. A set of novel materials with dyad and triad architectures based on 2 different discotic cores is reported and the conditions of emergence of such complex structures are investigated. The designed molecules associate together electron-donor triphenylene cores (D) and perylene or naphthalene diimides as acceptor moieties (A), both entities being linked via alkyl chain spacers. The evaluation in solution of their HOMO/LUMO energy levels by cyclic voltammetry demonstrates the preservation of the individual features of the D and A units. Their thermal and self-organization behaviors were studied by polarized-light optical microscopy, differential scanning calorimetry, temperature-dependent small-angle X-ray scattering and dilatometry, which permitted detailed investigation of the self-organization behaviour. These D-A compounds turned out to spontaneously self-organize into columnar mesophases at room temperature, with the D and A moieties segregated into either alternated stacks within mixed columns or in distinct columns, the latter providing an ideal configuration for 1D hole and electron transport pathways. In view of potential applications of the triad/dyad template, thin films of these self-organized materials were also probed by atomic force microscopy and grazing incidence X-ray scattering.
- Xiao, Yiming,Su, Xiaolu,Sosa-Vargas, Lydia,Lacaze, Emmanuelle,Heinrich, Beno?t,Donnio, Bertrand,Kreher, David,Mathevet, Fabrice,Attias, André-Jean
-
-
Read Online
- Synthesis and characterization of mesogenic triphenylene-perylene dyads with phenoxy-alkoxy linkers
-
Three novel triphenylene-perylene dyads with phenoxy-alkoxy linkers (PDI-OPhO-Cn-O- TP6, n = 6, 8, 10) have been synthesized and characterized by FT-IR, MS, 13C, and 1H NMR. The mesomorphic properties of these compounds were investigated by polarizing optical microscopy (POM) and differential scanning calorimetry (DSC). It was found that the dyads (PDI-OPhO-Cn-O-TP6, n = 6, 8) only showed thermotropic columnar mesophase in the heating process, while the dyad (PDI-OPhO-C10-O-TP6) showed enantiotropic columnar mesophase in both heating and cooling processes.
- Kong, Xiangfei,Dai, Shengping,Wang, Guixia,Zhang, Zhouyang,Zhang, Laiqi,Liao, Peihai,Liu, Wenting
-
-
Read Online
- Carborane-perylene diimide derivative and synthesis method thereof, sensing array based on derivative and preparation method and application of sensor array
-
The invention discloses a carborane-perylene diimide derivative and a synthesis method thereof, a sensing array based on the derivative and a preparation method and an application of the sensor array,and belongs to the technical field of small-molecular fluorescent sensing thin film materials. The carborane-perylene diimide derivative is placed in a solution, is assembled into a fiber structure with relatively large specific surface, and then is transferred to different substrate surfaces, so as to obtain the sensing array composed of a variety of fluorescent thin films; the sensing array canbe sensitive to sense six important drug gases, and drug samples have no need of any treatment; at the same time, through array combination, the interference of common interferents is eliminated thoroughly. The operation is simple, and the reaction conditions are mild. The prepared fluorescent sensing thin film has good stability and long service life, and is an excellent drug gas sensing thin film array. With combination use of the thin film and commercial fluorescent instruments, the drug gases can be sensitively detected. In addition, the drug gas special detection instrument can be developed through the device of the sensing thin film.
- -
-
Paragraph 0090; 0102; 0103; 0104
(2018/04/02)
-
- Heterologous perylene diimide arrays: Potential non-fullerene acceptors in organic solar cells
-
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
-
p. 8875 - 8882
(2017/09/11)
-
- Triphenylene-flexible bridge-perylene diimide binary compound and preparation method and application thereof
-
The invention discloses a triphenylene-flexible bridge-perylene diimide binary compound and a preparation method thereof and application of the compound serving as an organic solar cell active layer. Compared with the prior art, the triphenylene-flexible bridge-perylene diimide binary compound has the advantage of easily adjusting the liquid crystalline phase transformation temperature and temperature interval, and the compound has the application in photology, electrooptics and electronics, and particularly has the application in serving as the organic solar cell active layer. Please see the formula in the description.
- -
-
Paragraph 0088; 0089; 0090
(2017/01/02)
-
- The Relation between Packing Effects and Solid State Fluorescence of Dyes
-
The solid state fluorescence of diketopyrrolopyrrole dyes and perylene-3,4:9,10-tetracarboxylic bisimides with alkyl substituents are investigated and compared with noncovalent interactions.The latter are estimated by crystal structure analysis, heats and entropies of fusion and solubilities in organic solvents.Applications of the dyes are discussed.
- Langhals, H.,Demmig, St.,Potrawa, Th.
-
p. 733 - 748
(2007/10/02)
-