Photocleavage of Poly(methyl acrylate) with Centrally Located o-Nitrobenzyl Moiety: Influence of Environment on Kinetics

被引:24
作者
Lee, Michele E. [1 ]
Gungor, Eda [1 ]
Armani, Andrea M. [1 ]
机构
[1] Univ So Calif, Mork Family Dept Chem Engn & Mat Sci, Los Angeles, CA 90089 USA
关键词
PHOTOREMOVABLE PROTECTING GROUPS; REACTION-MECHANISMS; RESPONSIVE POLYMERS; COPOLYMERS BEARING; TRIGGERED RELEASE; SURFACE; LIGHT; HYDROGELS; DELIVERY; LINKERS;
D O I
10.1021/acs.macromol.5b01496
中图分类号
O63 [高分子化学(高聚物)];
学科分类号
070305 ; 080501 ; 081704 ;
摘要
We characterized the kinetics of a photo cleavable o-nitrobenzyl (ONB)-modified poly(methyl acrylate) in solution and in film. Using atom transfer radical polymerization, a single photolabile ONB group was incorporated into the center of the polymer chain, resulting in a clearly defined photoresponse. The photocleavage behavior was characterized in three difference solvents and in film, and it was fit to an exponential model. The dependence of the reaction rate constants and quantum efficiency on the interaction :parameter between the solvent and the polymer (chi(12)) and the molecular weight was investigated. Interestingly, as chi(12) decreased, the reaction rate increased and the quantum efficiency increased.
引用
收藏
页码:8746 / 8751
页数:6
相关论文
共 52 条
[11]   Triggered Release from Polymer Capsules [J].
Esser-Kahn, Aaron P. ;
Odom, Susan A. ;
Sottos, Nancy R. ;
White, Scott R. ;
Moore, Jeffrey S. .
MACROMOLECULES, 2011, 44 (14) :5539-5553
[12]   Doxorubicin loaded pH-sensitive micelle targeting acidic extracellular pH of human ovarian A2780 tumor in mice [J].
Gao, ZG ;
Lee, DH ;
Kim, DI ;
Bae, YH .
JOURNAL OF DRUG TARGETING, 2005, 13 (07) :391-397
[13]   Dual Photosensitive Polymers with Wavelength-Selective Photoresponse [J].
Garcia-Fernandez, Luis ;
Herbivo, Cyril ;
Arranz, Veronica San Miguel ;
Warther, David ;
Donato, Loic ;
Specht, Alexandre ;
del Campo, Aranzazu .
ADVANCED MATERIALS, 2014, 26 (29) :5012-5017
[14]   Photoselective Delivery of Model Therapeutics from Hydrogels [J].
Griffin, Donald R. ;
Kasko, Andrea M. .
ACS MACRO LETTERS, 2012, 1 (11) :1330-1334
[15]   Photodegradable Macromers and Hydrogels for Live Cell Encapsulation and Release [J].
Griffin, Donald R. ;
Kasko, Andrea M. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (31) :13103-13107
[16]   Linkers and cleavage strategies in solid-phase organic synthesis and combinatorial chemistry [J].
Guillier, F ;
Orain, D ;
Bradley, M .
CHEMICAL REVIEWS, 2000, 100 (06) :2091-2157
[17]   Wavelength-Selective Disruption and Triggered Release with Photo labile Polyelectrolyte Multilayers [J].
Gumbley, Patricia ;
Koylu, Damla ;
Pawle, Robert H. ;
Umezuruike, Bond ;
Spedden, Elise ;
Staii, Cristian ;
Thomas, Samuel W., III .
CHEMISTRY OF MATERIALS, 2014, 26 (03) :1450-1456
[18]   Photolabile protecting groups for nucleosides: Synthesis and photodeprotection rates [J].
Hasan, A ;
Stengele, KP ;
Giegrich, H ;
Cornwell, P ;
Isham, KR ;
Sachleben, RA ;
Pfleiderer, W ;
Foote, RS .
TETRAHEDRON, 1997, 53 (12) :4247-4264
[19]   Selective Anion-Induced Crystal Switching and Binding in Surface Monolayers Modulated by Electric Fields from Scanning Probes [J].
Hirsch, Brandon E. ;
McDonald, Kevin P. ;
Qiao, Bo ;
Flood, Amar H. ;
Tait, Steven L. .
ACS NANO, 2014, 8 (10) :10858-10869
[20]   Model studies for new o-nitrobenzyl photolabile linkers: Substituent effects on the rates of photochemical cleavage [J].
Holmes, CP .
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (08) :2370-2380