Abstract
New methacrylic copolymers, bearing in the side chain spiropyran moieties and/or the optically-active (S)-3-hydroxy pyrrolidinyl group linked through the nitrogen atom to an azopyridine chromophore, along with an opportune molar content of methyl methacrylate co-units, have been prepared by radical polymerization of the corresponding monomers. The resulting macromolecules have been fully characterized with particular attention to the study of their thermal stability, optical activity, chiroptical and photoinduced properties. In the presence of acid, it is possible to modulate the protonation of the azopyridine groups by photo-isomerization (with UV and/or Vis light) of the spiropyran component. The resulting signal communication between these macromolecular switches can be monitored by UV-VIS as well as CD spectroscopy and is completely reversible and reproducible. The results are discussed in terms of copolymer composition and different cooperative behaviour, which lead to a variation of interactions between spiropyran and azoaromatic chromophores and reveal that the best proton transfer is actually obtained in the random terpolymer with lower amounts of co-units of spiropyran and azopyridine chromophores in the side chain, which displays improved sensitivity to proton-transfer process and, in addition, exhibits good stability to repeated cycles of irradiation with UV and Vis light.
| Original language | English |
|---|---|
| Pages (from-to) | 5638-5646 |
| Number of pages | 9 |
| Journal | Polymer |
| Volume | 50 |
| Issue number | 24 |
| DOIs | |
| State | Published - Nov 16 2009 |
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Keywords
- Azopyridine
- Polymeric chiroptical switches
- Spiropyran
ASJC Scopus subject areas
- Organic Chemistry
- Polymers and Plastics
Cite this
Optical and chiroptical switches based on photoinduced photon and proton transfer in copolymers containing spiropyran and azopyridine chromophores in their side chains. / Angiolini, L.; Benelli, T.; Giorgini, L.; Raymo, Francisco.
In: Polymer, Vol. 50, No. 24, 16.11.2009, p. 5638-5646.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Optical and chiroptical switches based on photoinduced photon and proton transfer in copolymers containing spiropyran and azopyridine chromophores in their side chains
AU - Angiolini, L.
AU - Benelli, T.
AU - Giorgini, L.
AU - Raymo, Francisco
PY - 2009/11/16
Y1 - 2009/11/16
N2 - New methacrylic copolymers, bearing in the side chain spiropyran moieties and/or the optically-active (S)-3-hydroxy pyrrolidinyl group linked through the nitrogen atom to an azopyridine chromophore, along with an opportune molar content of methyl methacrylate co-units, have been prepared by radical polymerization of the corresponding monomers. The resulting macromolecules have been fully characterized with particular attention to the study of their thermal stability, optical activity, chiroptical and photoinduced properties. In the presence of acid, it is possible to modulate the protonation of the azopyridine groups by photo-isomerization (with UV and/or Vis light) of the spiropyran component. The resulting signal communication between these macromolecular switches can be monitored by UV-VIS as well as CD spectroscopy and is completely reversible and reproducible. The results are discussed in terms of copolymer composition and different cooperative behaviour, which lead to a variation of interactions between spiropyran and azoaromatic chromophores and reveal that the best proton transfer is actually obtained in the random terpolymer with lower amounts of co-units of spiropyran and azopyridine chromophores in the side chain, which displays improved sensitivity to proton-transfer process and, in addition, exhibits good stability to repeated cycles of irradiation with UV and Vis light.
AB - New methacrylic copolymers, bearing in the side chain spiropyran moieties and/or the optically-active (S)-3-hydroxy pyrrolidinyl group linked through the nitrogen atom to an azopyridine chromophore, along with an opportune molar content of methyl methacrylate co-units, have been prepared by radical polymerization of the corresponding monomers. The resulting macromolecules have been fully characterized with particular attention to the study of their thermal stability, optical activity, chiroptical and photoinduced properties. In the presence of acid, it is possible to modulate the protonation of the azopyridine groups by photo-isomerization (with UV and/or Vis light) of the spiropyran component. The resulting signal communication between these macromolecular switches can be monitored by UV-VIS as well as CD spectroscopy and is completely reversible and reproducible. The results are discussed in terms of copolymer composition and different cooperative behaviour, which lead to a variation of interactions between spiropyran and azoaromatic chromophores and reveal that the best proton transfer is actually obtained in the random terpolymer with lower amounts of co-units of spiropyran and azopyridine chromophores in the side chain, which displays improved sensitivity to proton-transfer process and, in addition, exhibits good stability to repeated cycles of irradiation with UV and Vis light.
KW - Azopyridine
KW - Polymeric chiroptical switches
KW - Spiropyran
UR - http://www.scopus.com/inward/record.url?scp=70449133705&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=70449133705&partnerID=8YFLogxK
U2 - 10.1016/j.polymer.2009.10.013
DO - 10.1016/j.polymer.2009.10.013
M3 - Article
VL - 50
SP - 5638
EP - 5646
JO - Polymer
JF - Polymer
SN - 0032-3861
IS - 24
ER -