Synthesis of acridinedione derivatives as laser dyes

Abstract

Synthesis of 9‐alkyl, 10‐alkyl, 9,10‐dialkyl, and 10‐aryl‐3,4,6,7,9,10‐hexahydro‐1,8(2H,5H)acridinedione (2a–r) are described as a new class of laser dyes. Reactions of diamines with methylene bis(cyclohexane‐1,3‐dione) yielded the respective bisacridinediones (3a–e). These dyes lase around 478–494 nm and are compared with the standard dye coumarin‐102. © 1996 John Wiley & Sons, Inc.

3,3,6,6-Tetramethyl-9-(2-nitrophenyl)-3,4,5,6,9,10-hexahydroacridine-1,8(2H,7H)-dione

“…Unexpectedly, the condensation product was not compound (3) as was reported previously (Martinez et al, 1995), but the tetraketone (4). This finding was supported not only by means of ~H NMR spectroscopy and MS spectrometry, but also by similar dimeric structures found in the literature (Greenhill, 1977;Shanmugasundram, Murugan, Ramakrishnan, Srividya & Ramamurthy, 1996). It may be noted that compound (4) is a common starting material for the preparation of compounds (5) Symmetry code: (i) ½ -x, y -½, -½ -z.…”

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

“…Acridine-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].…”

Crystalstructure of 1,3-bis[3,3,6,6-tetramethyl-3,4,6,7,9,1 0 -hexahydro-1,8 ( 2H,5H) -acridinedione-9-yl] benzene, C40H48N2O4

“…Acridine-l,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].…”