Theoretical and experimental investigation on the spectroscopic properties of indigo dye

Amat, Anna; Rosi, Francesca; Miliani, Costanza; Sgamellotti, Antonio; Fantacci, Simona

doi:10.1016/j.molstruc.2010.11.046

Cited by 63 publications

(61 citation statements)

References 44 publications

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“…As a consequence, the spectral changes associated to different shades could be interpreted as due to the colorant dilution [64], or as induced by dye alteration processes. Indigotin is already reported to be particularly lightfast [69] and highly sensitive to ozone [59,70,71], leading to a bluish-grey appearance and to modifications of its spectral profile. This induces a reflectance maximum shift toward longer wavelengths (closer to or even overlapping the green spectral range) associated with no relevant modifications of absorption maximum.…”

Section: Blue Huesmentioning

confidence: 99%

Non-invasive study of natural dyes on historical textiles from the collection of Michelangelo Guggenheim

Ferri

Tripodi

Martignon

et al. 2018

Spectrochimica Acta Part A: Molecular and Biomolecular Spectros

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a b s t r a c t a r t i c l e i n f oA selection of historical textile fragments from the Venetian art dealer Moisè Michelangelo Guggenheim collection, ranging from XV to XVIII century, has been investigated by means of non-invasive techniques in order to reveal the coloring materials. Imaging was preliminarily used to visually investigate the selected artwork fragments in order to investigate their structure and conservation conditions; Fiber Optics Reflectance Spectroscopy (FORS) allowed recognizing the main natural dyestuffs, such as indigotin and anthraquinones-based compounds, except the yellow ones, difficultly identifiable when using this non-invasive technique. Collected spectroscopic data have been also elaborated by using a clustering algorithm that permitted to group collected spectra on the basis of similar properties and evidencing their inflection point wavelength as the most influencing feature.

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Section: Blue Huesmentioning

confidence: 99%

Non-invasive study of natural dyes on historical textiles from the collection of Michelangelo Guggenheim

Ferri

Tripodi

Martignon

et al. 2018

Spectrochimica Acta Part A: Molecular and Biomolecular Spectros

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“…[ 24,26 ] Indeed, the calculated plots for epindolidione are very similar to those of indigo itself. [ 27 ] The addition of halogens para to the nitrogen groups is thus expected, according to the H-chromophore model, to infl uence primarily the HOMO. This is seen in the isodensity plots, where indeed charge density is localized over the halogens in the HOMO but not the LUMO orbitals.…”

Section: Optical Propertiesmentioning

confidence: 99%

Epindolidiones—Versatile and Stable Hydrogen‐Bonded Pigments for Organic Field‐Effect Transistors and Light‐Emitting Diodes

Głowacki

Romanazzi

Yumusak

et al. 2014

Adv Funct Materials

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1wileyonlinelibrary.com IntroductionHydrogen-bonded organic pigments are a class of materials familiar from applications in the colorant industry, where they fi nd widespread use as materials for robust outdoor paints, cosmetics, and printing inks. [ 1,2 ] Indigo, a natural product, is the oldest and still most widely produced organic dye and pigment ( Figure 1 ). [ 3 ] The intermolecular -NH … O = hydrogen bonding that characterizes indigo is exploited in most of the synthetic hydrogen-bonded pigments as well. This class of materials has proven to be nontoxic and safe for humans, and is considered safer than even several classes of food dyes. [ 4 ] Hydrogen-bonding as a supramolecular engineering tool is useful to control self-assembly and highly relevant to aqueous and biochemical systems. [ 5,6 ] Recently, we have found that indigo, [ 7 ] and some of its derivatives [ 8,9 ] demonstrate ambipolar transport in organic fi eldeffect transistors (OFETs), with mobility ranging from 0.01-0.4 cm 2 V -1 s -1 . We Epindolidiones-Versatile and Stable Hydrogen-Bonded Pigments for Organic Field-Effect Transistors and Light-Emitting DiodesEric Daniel Głowacki , * Giuseppe Romanazzi , Cigdem Yumusak , Halime Coskun , Uwe Monkowius , Gundula Voss , Max Burian , Rainer T. Lechner , Nicola Demitri , Günther J. Redhammer , Nevsal Sünger , Gian Paolo Suranna and Serdar Sariciftci Hydrogen-bonded pigments are remarkably stable high-crystal lattice energy organic solids. Here a lesser-known family of compounds, the epindolidiones, which demonstrates electronic transport with extraordinary stability, even in highly demanding aqueous environments, is reported. Hole mobilities in the range 0.05-1 cm 2 V -1 s -1 can be achieved, with lower electron mobilities of up to 0.1 cm 2 V -1 s -1 . To help understand charge transport in epindolidiones, X-ray diffraction is used to solve the crystal structure of 2,8-difl uoroepindolidione and 2,8-dichloroepindolidione. Both derivatives crystallize with a linear-chain H-bonding lattice featuring two-dimensional π-π stacking. Powder diffraction indicates that the unsubstituted epindolidione has very similar crystallinity. All types of epindolidiones measured here display strong low-energy optical emission originating from excimeric states, which coexists with higher-energy fl uorescence. This can be exploited in light-emitting diodes, which show the same hybrid singlet and low-energy excimer electroluminescence. Low-voltage FETs are fabricated with epindolidione, which operate reliably under repeated cyclic tests in different ionic solutions within the pH range 3-10 without degradation. Finally, in order to overcome the insolubility of epindolidiones in organic solvents, a chemical procedure is devised to allow solution-processing via the introduction of suitable thermolabile solubilizing groups. This work shows the versatile potential of epindolidione pigments for electronics applications.

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“…In our infrared spectrum from a paint layer a series of bands are identified: 1626 cm - 25,29 and with our own reference spectra of Isatis Tinctoria L. (Blue Pastel from Languedoc) and Indigofera Tinctoria L. (from Mexico). We observe that the spectra from the Indigofera Tinctoria L. dye shows more sharp and clear bands than that from Isatis Tinctoria L. The IR spectrum of the paint compares better to those of Isatis Tinctoria L. (Fig.…”

Section: Indigomentioning

confidence: 84%

“…It can be obtained from a great variety of plants whose leaves contain indigo precursors such as indoxyl-β-D-glucoside (indican) and indoxyl-5-ketoglucomate (isatan B). These substances are soluble in water and, through a process of an enzymatic fermentation (β-glucosidase) and later oxidation with atmospheric oxygen, are transformed into a blue substance namely, indigo [23][24][25][26][27][28][29] .…”

Section: Indigomentioning

confidence: 99%

“…Recent work by Amat et al 29 on spectroscopic properties of indigo dye assigns the infrared experimental bands to the functional groups and those to the theoretical spectrum. In our infrared spectrum from a paint layer a series of bands are identified: 1626 cm - 25,29 and with our own reference spectra of Isatis Tinctoria L. (Blue Pastel from Languedoc) and Indigofera Tinctoria L. (from Mexico).…”

Section: Indigomentioning

confidence: 99%

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New insights on blue pigments used in 15th century paintings by synchrotron radiation-based micro-FTIR and XRD

et al. 2014

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The blue pigments used on altarpieces in 15 th Century in Catalonia and Crown of Aragon are principally the azurite mineral. To a lesser extent lapis lazuli, also of mineral origin and occasionally, in the background areas, outlining the figures, and for the chromatic ground layer, indigo, were used. Data from several altarpieces belonging to well-known artists of the time is presented. Synchrotron radiation X-ray diffraction (SR-XRD), micro-infrared spectroscopy (µ-FTIR), synchrotron radiation micro-infrared spectroscopy (µSR-FTIR), Raman spectroscopy, scanning electron microscopy with Xray microanalysis (SEM-EDS) are used. X-ray diffraction and infrared spectroscopy in association with synchrotron radiation have shown to be especially interesting due to the micron spot sizes, high brilliance and energy tunability which help to obtain good separation of the signals coming from different phases/substances and their localization in the various paint layers. Examples are presented which illustrate the potential of each analytical technique for the identification of this kind of materials in the 15 th century paintings. The natural origin and composition of the pigments and its distribution in the paint layers are determined and some correlations with other contemporary paintings obtained. Finally, the alteration compounds related to blue pigments are determined in each case.

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Theoretical and experimental investigation on the spectroscopic properties of indigo dye

Cited by 63 publications

References 44 publications

Non-invasive study of natural dyes on historical textiles from the collection of Michelangelo Guggenheim

Non-invasive study of natural dyes on historical textiles from the collection of Michelangelo Guggenheim

Epindolidiones—Versatile and Stable Hydrogen‐Bonded Pigments for Organic Field‐Effect Transistors and Light‐Emitting Diodes

New insights on blue pigments used in 15th century paintings by synchrotron radiation-based micro-FTIR and XRD

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