Novel Perylene Chromophores Obtained by a Facile Oxidative Cyclodehydrogenation Route

Abstract

New perylene chromophores, phenyl-substituted diindeno[1,2,3-cd:1',2',3'-lm]perylenes 5a,b and 4,4',7,7'-tetraphenyldiacenaphtho[1,2-k:1',2',k']diindeno[1,2,3-cd:1',2',3'-me]perylenes 22a,b, have been synthesized from substituted fluoranthene derivatives 3a,b and 4a,b by means of a surprisingly simple oxidative cyclodehydrogenation reaction. The resulting chromophores, when substituted with alkyl chains at the periphery, show good solubility in organic solvents, and a full characterization of the novel red, green, and blue dyes by field-desorption mass spectrometry, UV/Vis and 1H and 13C NMR spectroscopy becomes possible.

Synthesis and Transistor Properties of Asymmetric Oligothiophenes: Relationship between Molecular Structure and Device Performance

“…2‐Decylthiophene ( 5 ) was synthesized by the reaction of ortho ‐lithiated thiophene with 1‐bromodecane and was used for the synthesis of the boronic ester 6 3b. 4‐Bromodecylbenzene ( 7 ) was readily available by Friedel–Crafts acylation of bromobenzene, followed by a Wolff–Kishner reduction 11. Compound 7 was then esterified with 2‐isopropyl‐4,4,5,5‐tetramethyl‐1,2,3‐dioxabolane in the presence of n BuLi to give 8 .…”

“…[3b] 4-Bromodecylbenzene (7) was readily available by Friedel-Crafts acylation of bromobenzene, followed by a Wolff-Kishner reduction. [11] Compound 7 was then esterified with 2-isopropyl-4,4,5,5-tetramethyl-1,2,3-dioxabolane in the presence of nBuLi to give 8.…”

Comparison of Oxidative Aromatic Coupling and the Scholl Reaction

“…The oxidation of sterically less‐congested 84 c and 84 d leads to the formation of polyaromatic hydrocarbons 86 c , d as a result of both inter‐ and intramolecular oxidative coupling (Scheme ) 109. 113…”

Synthesis and coordination chemistry of N-doped polyphenylenes

“…Acenaphthenequinone was purchased from Aldrich. 7,9-Diphenyl-8H-cyclopenta[l] acenaphthylen-8-one (1a) was prepared according to a literature procedure (Wehmeier et al 2001).…”

“…The presence of a fused 5-membered ring in the skeleton makes fluoranthene derivatives suitable for the preparation of curved molecules such as corannulene and semibuckminsterfullerene (Sygula & Rabidean, 1999). Fluoranthene derivatives can be cyclodehydrogenated to generate large aromatic sheets (Debad et al 1996& Wehmeier et al 2001. In this paper we describe the synthesis of new ligands (2a) and (2b) based on 8-azafluoranthene, and their complexes with molybdenum(0) and palladium (II).…”