Heteroatom-Annulated Perylenes: Practical Synthesis, Photophysical Properties, and Solid-State Packing Arrangement

Abstract

A practical strategy for the preparation of a series of heterocyclic annulated perylenes in good yields is presented. UV-vis absorption spectra indicate hypsochromic shift of the absorption maxima relative to the corresponding parent perylene. Single-crystal X-ray diffraction analysis reveals that they all adopt planar conformation, but the solid-state packing arrangements are significantly altered by annulation of various heterocycles.

Two new fluorescent heterocyclic perimidines: first syntheses, crystal structure, and spectral characterization

“…In compound 1, hypsochromic shift (negative fluorescent solvatochromism) 24 is noticed on changing the nature of solvent from non-polar to polar suggesting that this may be due to the apparent stabilization of the ground state through dipole-dipole interaction or a possible hydrogen bonding in polar solvents. On the other hand, a constant bathochromic shift 25 (positive fluorescent solvatochromism) is noticed in the fluorescence spectra of compound 2. This might be due to the absence of hydroxyl group in compound 2 and consequent hydrogen bonding interactions.…”

Donor/Acceptor Indenoperylene Dye for Highly Efficient Organic Dye-Sensitized Solar Cells

“…Further implementation of Pd-catalyzed Miyaura borylation under mild conditions converted 4 to phenylboronic acid pinacol ester 5 in excellent yield. Subsequent Suzuki-Miyaura cross-coupling of 5 and 3-bromo-1-(2-hexyldecyl)-1H-phenanthro [1,10,9,8-cdefg]-carbazole 17 produced key intermediate 6 in good yield. Then, 6 was implemented in a carbonyl addition reaction with (4-hexylphenyl)magnesium bromide 13b to generate a tertiary alcohol, which was not isolated and underwent intramolecular Friedel-Crafts cyclization with the aid of solid acid catalyst Amberlyst 15 to afford coplanar electron-donor 7.…”

Self-assembly, optical and electrical properties of five membered O- or S-heterocyclic annulated perylene diimides

“…The Liquid-crystalline PDI derivative exhibits an ordered columnar phase at room temperature in which the electron mobility exceeds 0.1 cm 2 V À1 s À1 [25]. Both O-PDI and S-PDI have significant electronic coupling between their heteroatom/heterocycles and PDI cores [26], and the cyclohexyl end-capping groups increase the steric bulkiness to the periphery of the two molecules [27]. So, despite the extension of the aromatic core of perylene, these two PDI derivatives are soluble in common organic solvents, and thus allowed us to compare their UVeVis in a range of solvents (cyclohexane, ethylene acetate, tetrahydrofuran, dichloromethane and dimethylformamide) as shown in Fig.…”