The effects of cyclic terminal groups in di- and tri-arylmethane dyes. Part 2.1 Steric and electronic effects in derivatives of Victoria Blue

Abstract

The effects of N-alkyl and heterocycloalkyl substituents on the light absorption properties of a range of novel dyes based on the 1-naphthyl analogue of Crystal Violet, Victoria Blue, have been investigated. Interaction between the N-terminal group and the peri-hydrogen atom on the naphthyl residue can result in deconjugation of the former, whereupon the dyes exhibit Malachite Green character. Such steric influences are correlated with 1 H NMR data.

Copper‐Catalyzed Electrophilic Amination of Functionalized Diarylzinc Reagents.

“…The title compound was prepared according to General Procedure E using 1-iodo-naphthalene (0.1398 g, 0.55 mmol), 4-(benzoyloxy)morpholine (0.0518 g, 0.25 mmol), and copper(I) trifluoromethanesulfonate benzene complex ([CuOTf] 2 ⋅C 6 H 6 , 0.0016 g, 0.0031 mmol) to yield 4-(naphthalen-1-yl)-morpholine (0.0481 g, 0.23 mmol, 90% yield) as a white solid. The 1 H NMR spectrum was consistent with that reported in the literature 12. The title compound was prepared according to General Procedure E using 4-iodoanisole (0.1287 g, 0.55 mmol), 4-(benzoyloxy)morpholine (0.0518 g, 0.25 mmol), and copper(I) trifluoromethanesulfonate benzene complex ([CuOTf] 2 ⋅C 6 H 6 , 0.0016 g, 0.0031 mmol) to yield 4-(4-methoxyphenyl)-morpholine (0.0403 g, 0.21 mmol, 83% yield) as a white solid.…”

Untitled

“…VBBO, VBR, VBB and 1-octanol were purchased from Aldrich Chemicals (Poole, Dorset, UK) and were used without further purification. The synthesis of new photosensitizers followed an established procedure has been reported elsewhere (Guinot, Hepworth and Wainwright, 1998). Elemental analysis for the new photosensitizers were correct and purity was confirmed by high performance liquid chromatography and high field 1 H nuclear magnetic resonance spectroscopy ( 1 H NMR) (Brüker WM250 spectrometer).…”

Synthesis and electronic absorption spectra of some novel methoxy half-analogs of Malachite Green and Brilliant Green

“…Previously, electronic absorption spectra of a comprehensive range of related methoxy half-analogs of Michler's Ketone [1], Michler's Hydrol Blue [2], Malachite Green [3], and Victoria Blue [4] has been studied. Now the major part of the present work has been devoted to the study of the absorption spectra of a series of novel triarylmethane dyes (II-V) containing Kairoline [5,6], Julolidine [7], and N-2-Cynoethyl-1,2,3,4-tetrahydroquinoline [8] groups.…”