The Effect of Polymer Composition and Structure on the Photo-Fries Rearrangement

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ProQuest, 2008 - 90 стор.
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Varying constraint by tethering aryl esters to the polymer backbone at the ester group, tethering aryl esters to the polymer backbone through the aryl group and varying the Tg of polymers had no effect on the rate of the photo-Fries rearrangement. The hydration state of hydrophilic copolymers had no effect on conversion but did increase formation of cage escape products and changed the ratio of products formed. Decreasing the proximity of aryl ester units relative to one another lead to increased ultimate conversion in the rearrangement. Altering from a carbon to siloxane polymer backbone may have had an effect on the initial rate of rearrangement but the effect could not be isolated from other variables (proximity and Tg).
 

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Introduction
1
Acetoxybenzene undergoing the photoFries rearrangement
2
Detailed mechanism of photoFries rearrangement
3
Comparison of thermal and photochemical catalyzed Fries rearrangements
4
Representation of the structure ofZSM5 zeolite
6
Structure of Nafion
7
Structure of βcyclodextrin
8
Rearrangement of βcyclodextrin naphthyl ester complexes
9
Synthesis of polypacetoxystyrenecohydroxyethyl methacrylate
32
Synthesis of pacetoxystyrene functionalized polysiloxane
33
Phenyl 3butenoate functionalized polysiloxane
35
Synthesis of phenyl 3butenoate functionalized polysiloxane
36
Synthesis of naphthalene1yl benzoate
38
Initial polymerization conditions for HEMA copolymers
41
Overlaid FTIR Spectra ofPPA at 0 30 and 60 minutes
43
Comparison of constraint of PAS and PPA
44

Styrenebased amphiphilic homopolymer polymer A utilized by Ramamurthy
11
PhotoFries rearrangement of polycarbonate
13
PhotoFries rearrangement ofpolypacetoxystyrene and polypformyloxystyrene
15
Novel photoFries active polymers synthesized by Kern
16
FTIR spectra of PAS and polybicyclo2 2 1hept5ene2carboxylic acid phenyl ester undergoing the photoFries rearrangement
17
Cauchy fit curve obtained from PAS
18
Additional photoFries active polymers studied by Kern
19
Refractive index change associated with photoFries rearrangement of acetoxybenzene
20
Structure of polynaphthylene1yl 4vinylbenzoate
21
Energy transfer observed between polysodium styrenesolfonateco2vinylfluorene and 1naphthyl acetate
22
Antenna effect in the rearrangement of naphthalene1yl benzoate in the presence offluorene
23
Experimental
24
Synthesis of polypacetoxystyrene
26
Synthesis of polyphenyl acrylate
27
Synthesis of polypacetoxystyrenecobutyl acrylate
28
Synthesis of polyphenyl acrylatecobutyl acrylate
29
Synthesis of polyphenyl acrylatecohydroxyethyl methacrylate
30
Conversion of PAS and PPA versus time
45
Conversion of PAS and ASBA verses time
46
Conversion of PPA PAEA and PABA verses time
47
Yield ofortho and para products in PPA and PAEA rearrangements
48
Conversion of dry and water swollen ASHEMA over time
49
Yield ofortho product in ASHEMA rearrangement
50
Yield ofortho and para products in PAHEMA rearrangement
51
Difference in proximity demonstrated between PAS and PABA
54
Conversion of PAS and ASSiO
55
Refractive Index Changes
56
Cauchy fit curves showing n of PAS with increasing irradiation time with Kerns data shown in inset plot
57
Cauchyfit curves showing n in PPA with increasing irradiation time
58
Cauchyfit curves showing n in PAEA with increasing irradiation time
59
Refractive indices of isolated aryl ester groups dyads and triads calculated from group contributions
61
Linear dose dependent modulation of n in PAEA
62
PhotoFries rearrangement of naphthalene1yl benzoate in the presence of increasing amounts offluorene
63
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