Optically active polymethacrylates with side-chain l -lactic acid residues connected to push–pull azobenzene chromophores

Angiolini, Luigi; Caretti, Daniele; Giorgini, Loris; Salatelli, Elisabetta; Altomare, Angelina; Carlini, Carlo; Solaro, Roberto

doi:10.1016/s0032-3861(99)00701-6

Cited by 35 publications

(29 citation statements)

References 20 publications

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“…However, it is reasonable to attribute this enhancement mainly to a larger presence of ordered chiral conformations in solution. It is also worth noting that the optical activity at the sodium D line exhibited by poly[(S)-MAP] in CHCl 3 solution is noticeably higher than those previously found for poly(MOSI) 4 and poly(MLO), 2 indicative of an important role played by the pyrrolidine moiety in this system. As expected, the optical rotation at 589 nm of poly[(S)-MAP-N] could not be measured, due to the elevated light absorbance of the conjugated chromophore.…”

Section: Synthesis and Characterization Of Poly[(s )-Map] And Poly[(smentioning

confidence: 59%

Synthesis and chiroptical properties of optically active photochromic methacrylic polymers bearing in the side chain the (S)-3-hydroxypyrrolidinyl group conjugated with thetrans-azoaromatic chromophore

Angiolini

Caretti

Giorgini

et al. 1999

J. Polym. Sci. A Polym. Chem.

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Novel optically active polymethacrylates, namely poly[(S)‐3‐methacryloyloxy‐1‐(4‐azobenzene)pyrrolidine] and poly[(S)‐3‐methacryloyloxy‐1‐(4′‐nitro‐4‐azobenzene)pyrrolidine], have been synthesized by radical polymerization of the corresponding monomers, prepared in turn through a synthetic route preserving the asymmetric center by any racemization reaction. These homopolymers are characterized by the presence in the side chain of an optically active pyrrolidinyl ring linked to the trans‐azoaromatic system through the nitrogen atom. The optical activity of the polymers in solution appears much higher than that observed with the low molecular weight models, purposely synthesized for comparison. Circular dichroism spectra of the synthesized products demonstrated that, in solution, the macromolecules assume highly homogeneous conformations with a prevailing chirality to a larger extent with respect to analogous systems previously investigated. © 1999 John Wiley & Sons, Inc. J Polym Sci A: Polym Chem 37: 3257–3268, 1999

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Section: Synthesis and Characterization Of Poly[(s )-Map] And Poly[(smentioning

confidence: 59%

Synthesis and chiroptical properties of optically active photochromic methacrylic polymers bearing in the side chain the (S)-3-hydroxypyrrolidinyl group conjugated with thetrans-azoaromatic chromophore

Angiolini

Caretti

Giorgini

et al. 1999

J. Polym. Sci. A Polym. Chem.

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“…[14,17] Rate constants for the trans → cis and cis → trans isomerization of MPABA were found to be 7.59 × 10 -4 and 14.68 × 10 -4 s -1 , respectively, which is quite comparable with other literature values. [18] …”

Section: Synthesis and Photoisomerization Properties Of The Functionamentioning

confidence: 99%

The Fabrication of a Photoresponsive Molecularly Imprinted Polymer for the Photoregulated Uptake and Release of Caffeine

2006

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“…These results are due to the decrease of the content of azobenzene in polymers and/or the accelerating effect of the chiral groups in the comb-like polymers. [15][16][17][18][19] The high decrease rate of polymer P 8 may be due to the accelerating effect of the neighboring chiral groups for the molar ratio of azobenzene and chiral group(cholesteryl) is ϳ 1 : 9 in polymer P 8 . The influence factors on trans-cis isomerization of azobenzene are under further investigation.…”

Section: Photochemical Characterization Of M2 and Polymersmentioning

confidence: 99%

Synthesis and properties of photochromic cholesteric liquid crystalline polysiloxane containing chiral mesogens and azobenzene photochromic groups

Zhi

Zhang

Zang

et al. 2002

J of Applied Polymer Sci

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A series of novel thermotropic side-chain liquid crystalline polymers(P 0 -P 12 ) were synthesized by grafting copolymerization of mesogenic monomer cholesteryl undecylenate (M1) and photochromic monomer 4-allyoxy-4Ј-nitroazobenzene (M2) on polymethylhydrosiloxane. The chemical structures of polymers were characterized by infrared (IR) and ultraviolet (UV) spectroscopy. Differential scanning calorimetry (DSC) and thermogravimetric analysis (TGA) were used to measure the thermal properties of those polymers, and the mesogenic properties were characterized by polarized optical micrograph, DSC, wide-angle X-ray diffraction and small-angle X-ray scattering. The glass transition temperatures (T g s) of the polymers increased from P 0 to P 4 and decreased from P 5 to P 12 . The clearing point temperatures (T i s) of the polymers P 1 -P 12 were lower than that of P 0 , but increased from P 1 to P 4 and decreased from P 5 to P 12 . They showed thermotropic liquid crystalline properties in a broad mesogenic region at temperatures Ͼ100°C. The polymers P 0 -P 8 exhibited a cholesteric mesophase with oily streaks and lined texture, and polymers P 9 -P 12 showed a chiral smectic mesogenic phase with a layered texture. All of the polymers were thermally stable to ϳ 320°C. The UV-induced trans-cis photoisomerization was investigated for the azo monomer and polymers P 8 and P 12 . The solution of the azo monomer and liquid crystalline polymers P 8 and P 12 can undergo photoisomerization, and the environments of the azo group were responsible for the aforementioned photochemical process.

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Optically active polymethacrylates with side-chain l -lactic acid residues connected to push–pull azobenzene chromophores

Cited by 35 publications

References 20 publications

Synthesis and chiroptical properties of optically active photochromic methacrylic polymers bearing in the side chain the (S)-3-hydroxypyrrolidinyl group conjugated with thetrans-azoaromatic chromophore

Synthesis and chiroptical properties of optically active photochromic methacrylic polymers bearing in the side chain the (S)-3-hydroxypyrrolidinyl group conjugated with thetrans-azoaromatic chromophore

The Fabrication of a Photoresponsive Molecularly Imprinted Polymer for the Photoregulated Uptake and Release of Caffeine

Synthesis and properties of photochromic cholesteric liquid crystalline polysiloxane containing chiral mesogens and azobenzene photochromic groups

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