Abstract
An oxazine auxochrome and a carbazole chromophore can be integrated within the same covalent skeleton to generate a halochromic molecular switch. Upon addition of acid, the oxazine ring opens to bring the carbazole fragment in conjugation with a 3H-indolium cation. This structural transformation shifts the main absorption of the carbazole chromophore from the ultraviolet to the visible region and, as a result, is accompanied by the appearance of an intense red color. This species can be formulated into an ink to print colored patterns on conventional paper. Upon treatment with base, however, the oxazine ring closes to restore the initial colorless state and erase the printed pattern. In fact, the very same sheet of paper can be recycled for multiple printing and erasing steps. Thus, this structural design for switchable inks can evolve into viable operating principles to enable innovative printing technologies and reduce drastically paper consumption.
| Original language | English |
|---|---|
| Pages (from-to) | 71-73 |
| Number of pages | 3 |
| Journal | Dyes and Pigments |
| Volume | 106 |
| DOIs | |
| State | Published - Jul 1 2014 |
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Keywords
- Carbazole
- Halochromism
- Heterocycle
- Molecular switch
- Oxazine
- Switchable ink
ASJC Scopus subject areas
- Chemical Engineering(all)
- Process Chemistry and Technology
Cite this
Saving paper with switchable ink. / Garcia-Amorós, Jaume; Swaminathan, Subramani; Raymo, Francisco.
In: Dyes and Pigments, Vol. 106, 01.07.2014, p. 71-73.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Saving paper with switchable ink
AU - Garcia-Amorós, Jaume
AU - Swaminathan, Subramani
AU - Raymo, Francisco
PY - 2014/7/1
Y1 - 2014/7/1
N2 - An oxazine auxochrome and a carbazole chromophore can be integrated within the same covalent skeleton to generate a halochromic molecular switch. Upon addition of acid, the oxazine ring opens to bring the carbazole fragment in conjugation with a 3H-indolium cation. This structural transformation shifts the main absorption of the carbazole chromophore from the ultraviolet to the visible region and, as a result, is accompanied by the appearance of an intense red color. This species can be formulated into an ink to print colored patterns on conventional paper. Upon treatment with base, however, the oxazine ring closes to restore the initial colorless state and erase the printed pattern. In fact, the very same sheet of paper can be recycled for multiple printing and erasing steps. Thus, this structural design for switchable inks can evolve into viable operating principles to enable innovative printing technologies and reduce drastically paper consumption.
AB - An oxazine auxochrome and a carbazole chromophore can be integrated within the same covalent skeleton to generate a halochromic molecular switch. Upon addition of acid, the oxazine ring opens to bring the carbazole fragment in conjugation with a 3H-indolium cation. This structural transformation shifts the main absorption of the carbazole chromophore from the ultraviolet to the visible region and, as a result, is accompanied by the appearance of an intense red color. This species can be formulated into an ink to print colored patterns on conventional paper. Upon treatment with base, however, the oxazine ring closes to restore the initial colorless state and erase the printed pattern. In fact, the very same sheet of paper can be recycled for multiple printing and erasing steps. Thus, this structural design for switchable inks can evolve into viable operating principles to enable innovative printing technologies and reduce drastically paper consumption.
KW - Carbazole
KW - Halochromism
KW - Heterocycle
KW - Molecular switch
KW - Oxazine
KW - Switchable ink
UR - http://www.scopus.com/inward/record.url?scp=84897869729&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=84897869729&partnerID=8YFLogxK
U2 - 10.1016/j.dyepig.2014.02.019
DO - 10.1016/j.dyepig.2014.02.019
M3 - Article
AN - SCOPUS:84897869729
VL - 106
SP - 71
EP - 73
JO - Dyes and Pigments
JF - Dyes and Pigments
SN - 0143-7208
ER -