Revisiting Perkin's dye(s): the spectroscopy and photophysics of two new mauveine compounds (B2 and C)

Abstract

Two new components have been identified in an early sample prepared according to the original recipe of Perkin, and perhaps even by Perkin himself around 1860--a new isomer of Perkin's mauveine B (designated as mauveine B2) together with a new mauveine compound (mauveine C)--and these compounds were synthesized again using starting materials chosen to reproduce Perkin's original synthesis and isolated by HPLC-DAD, identified by (1)H NMR, MS and their spectroscopic (UV/Vis and emission) and photophysical behaviour investigated.

A Study in Mauve: Unveiling Perkin's Dye in Historic Samples

“…[14,15] In their pioneering analysis of historic salt samples, obtained from the Science Museum (London) and from the then Zeneca archives at Blackley (Manchester) published by Otto Meth-Cohn and Mandy Smith in 1994, two compounds were considered to be the main chromophores, mauveine A (major compound) and B, C 26 and C 27 structures, respectively, see Scheme 1. [11] Later on, by using a modern synthesis, some of us verified [16] that it was possible to obtain pseudo-mauveine (C 24 ), mono (C 25 ), di-(C 26 ), tri-(C 27 ) and tetramethylated (C 28 ) derivatives by using aniline, o-toluidine and p-toluidine as starting materials, and depending on the ortho to para ratios, to also obtain different isomeric ratios. Two other compounds, mauveine B2 and C, C 27 and C 28 compounds, respectively, were then discovered during analysis.…”

“…Two other compounds, mauveine B2 and C, C 27 and C 28 compounds, respectively, were then discovered during analysis. [16] Figure 1. The Science Museums "Original Sample" of mauve (left).…”

Amphiphilic Hyperbranched Polymers: Synthesis and Host‐Guest Supermolecular Coloring Application

“…The orange precipitate was collected and dried under a vacuum at 40 °C overnight, producing HPTAM (1.656 g) with a yield of 61.0%. 1 …”

“…[ 1 ] Compared to pigments, dyes are commonly soluble in specifi c solvents, showing brighter colors, and better transparency and dispersion. Unfortunately, dyes can be easily released from colored objects, since the interactions between them are not strong enough.…”

“…Therefore, the dye released from colored objects is still a big challenge. 1 H and 13 C NMR spectra were obtained on a Varian Mercury plus 300 NMR spectrometer using CDCl 3 or DMSOd 6 as the solvent. Fourier Transform infrared (FTIR) spectra were recorded on a self-condensing vinyl polymerization (SCVP), reversible addition-fragmentation chain-transfer polymerization (RAFT), and a Menschutkin reaction, to synthesize an AHP which is composed of quaternary ammonium salt hydrophilic moieties and tunable hydrophobic segments.…”