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Issue 33, 2015
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Chromophoric materials derived from a natural azulene: syntheses, halochromism and one-photon and two-photon microlithography

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Abstract

In addition to their use as colorants in food and cosmetics, various natural dyes possess photophysical properties that could enable their use as modular building blocks for preparing eco-friendly and non-toxic chromophores. Among the natural pigments, guaiazulene holds great potential due to its unique optical and electronic properties. Thus, in order to explore and understand the properties of guaiazulene-containing chromophores, a series of 4-styrylguaiazulenes 3a–l were prepared by condensation of the C-4 methyl group of naturally-occurring guaiazulene 1 with various aromatic carboxaldehydes 2a–l. Treatment of these analogs 3a–l with a strong acid protonates the electron-rich C-3 position and reveals a reversible halochromic behavior where the optical energy gap responds predictably to the electron-donor strength and the degree of π-conjugation. Additionally, acid-doping is accompanied by efficient fluorescence switch-on, where 3e(H+) and 3g(H+) exhibited considerably higher fluorescence quantum yields than the neutral precursor. These properties facilitated the design of a new non-erasable 3D fluorescence readout (permanent or write-once read-many, WORM) system, which is comprised of a switch-on fluorescent guaiazulene-containing chromophore 3e and a commercially available iodonium photo-acid generator (PAG) in thin polymethyl methacrylate (PMMA) films.

Graphical abstract: Chromophoric materials derived from a natural azulene: syntheses, halochromism and one-photon and two-photon microlithography

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Publication details

The article was received on 22 May 2015, accepted on 28 Jun 2015 and first published on 01 Jul 2015


Article type: Paper
DOI: 10.1039/C5TC01459J
Citation: J. Mater. Chem. C, 2015,3, 8495-8503
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    Chromophoric materials derived from a natural azulene: syntheses, halochromism and one-photon and two-photon microlithography

    E. H. Ghazvini Zadeh, S. Tang, A. W. Woodward, T. Liu, M. V. Bondar and K. D. Belfield, J. Mater. Chem. C, 2015, 3, 8495
    DOI: 10.1039/C5TC01459J

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