Crystal structure of 1,3-bis[3,3,6,6-tetramethyl-3,4,6,7,9,10-hexahydro- 1,8(2H,5H)-acridinedione-9-yl]benzene, C40H48NO4

Abstract

Source of materialA mixture of dimedone (4 mmol) and isophthalaldehyde (1 mmol) was stirred at 313 K -323 K for 10 min. in aqueous methanol until the solution became cloudy, and the reaction mixture was then allowed to stand at room temperature overnight. The solid obtained was collected by filtration and crystallized from ethanol as pale yellow crystals (36 %), mp 511 K -513 K. To a solution of the latter (5 mmol) in acetic acid (10 ml) was added ammonium acetate (11 mmol). The reaction mixture was heated under reflux for 2h, cooled and poured over crashed ice. The solid obtained was then collected and crystallized from ethanol to give 1,3-bis [3,3,6,6-tetramethyl-3,4,6,7,9,10-hexahydro-1,8(2H,5H)-acridine dione-9-yl]benzene as pale yellow crystals (yield 48 %). DiscussionAcridine-1,8-dione dyes have been shown to have very high lasing efficiency [1,2] and are also interesting in view of the electrochemical behaviour of heterocyclic compounds [3]. They have been used as electron donors and electron acceptors [4][5][6] and in the photoinitiated polymerization of acrylates and methacrylates [7]. In addition to this, these compounds have long been known to be potent farmeshift mutagerns in viruses and bacteria [8].We report here the crystal structure of the novel 1,3-bis(acridinedione-9-yl)benzene. Bond lengths and angles of the acridine skeleton are in agreement with those of related acridine derivatives