Synthesis and Characterization of Liquid Crystalline Perylene Diimides

Abstract

Several polyoxyethylene-substituted perylene-3,4,9,10-tetracarboxyldiimides have been synthesized and characterized. Relative to other known perylene diimide derivatives, all of the present compounds have much lower melting points and much greater solubility in common solvents. Most of these compounds possess liquid crystalline properties over a wide range of temperatures, some of them even at room temperature and below. Some of the photophysical and self-organizing characteristics of these compounds are demonstrated, particularly with regard to the spontaneous formation of a highly crystalline black phase. Generalized correlations about the physical properties and the chemical structures of these new liquid crystalline compounds are discussed. Their unusual physical and photophysical properties have important implications for their use in a variety of electroactive and photovoltaic applications.

Hierarchical Assembly of Organic/Inorganic Building Molecules with π–π Interactions

“…Such red-shift phenomena have been reported in other assembled PD systems and have been attributed to the highly ordered molecular organization that allows more efficient p-p stacking and energy transport among the bridging PD moieties. [30][31][32][33][34][35][36] Figure 3 (right) shows the fluorescence spectra of PDBS solution and the assembled aggregates with different morphologies. Similarly, these aggregates show evidently red-shift as compared to PDBS spectrum in dilute solution.…”

Fluorescent macromolecular perylene diimides containing pyrene or indole units in bay positions

“…Both symmetric and unsymmetric derivatives of diimides have been extensively used in dye sensitized solar cells (DSSC) [11e14], organic light emitting diodes (OLED) [15], organic field effect transistors (OFED) [16], liquid crystal displays (LCD) [17], dye lasers [18], photosensitizers in chemical oxidations [7], photodynamic therapy [19] and DNA G-quadruplex stabilization [20e22].…”

Supramolecular Organization of $$\pi $$-Conjugated Oligomers

“…Therefore, one can introduce electron-withdrawing groups like halogens, nitro or carboximide groups (22-26) [102][103][104][105][106]. Naphthalene and perylene bisimides derivatives (25,26) are probably the most prominent compounds of this class with similarly high electron charge-carrier mobilities [107][108][109][110]. Another, strategy to access n-type semiconducting compounds is to introduce nitrogen atoms in the core of the aromatic system to reduce its electron density as for instance in compounds 27-31 [111][112][113][114][115][116][117][118][119][120].…”