Copyright
IIT Kharagpur
Abstract
Newly Developed Nonionic Photoacid Generators and Their Applications
Our main focus is to design and develop new types of nonionic photoacid generators (PAGs) for both carboxylic and sulfonic acids based on N-O bond cleavage chemistry. Further, we are also interested to investigate the applications of newly synthesized PAGs in polymer and surface chemistry.
With this intention, we have targeted N-hydroxy aromatic compounds such as N- phenylhydroxylamine, 1-acetylferroceneoxime, 1-hydroxy-2(1H)-quinolone, and N- hydroxyanthracene-1,9-dicarboxyimide (HADI) as PAGs, since they have weak N-O bond which can be easily cleaved by direct photolysis.
The thesis entitled “Newly Developed Nonionic Photoacid Generators and Their Applications” consists of five chapters. Chapter-1 provides the general introduction to Photoacid Generators (PAGs) and their applications. Chapter-2 explains in detail about the photophysical and photochemical properties of newly synthesized PAGs based on N-acyl-N- phenylhydroxylamines for carboxylic and sulfonic acids. Chapter-3 describes 1- acetylferroceneoxime based PAGs for both carboxylic and sulfonic acids. Chapter-4 elaborates the design and synthesis of 1-hydroxy-2(1H)-quinolone based PAGs and their applications in the construction of photoresponsive polymer surfaces. Chapter-5 describes in detail about the synthesis, photophysical and photochemical properties of newly designed fluorescent PAGs based on N-hydroxy anthracene-1,9-dicarboxyimide and their application towards the development of photoresponsive organosilica surface
OSO2R3
NHCOCH3 h254 nm
MeOH-H2O
OH NHCOCH3
+ R3SO3H
R3 = Sulfonic acid residue
+ R1CO2H N
O H3C
O R1 O
NH O H3C MeOH-H2O h254 nm
R1 = Carboxylic acid residue
Fe O
CH3
5 h 310 nm
MeOH-H2O R1CO2H
R1 = carboxylic acid residue
+
Fe N
CH3
O O R1
Fe N
CH3
O S O O
R2 Fe O
CH3 h 310 nm
MeOH-H2O) + R2SO3H
R2 =sulfonic acid residue
h 310 nm MeOH-H2O
+ R2SO3H
R1 = Sulfonic acid residue
+R1CO2H h 310 nm
R1 = Carboxylic acid residue
N O
O O
R1
N O
OS O
R2 O
N
H O
N
H O
MeOH-H2O
N O
O
O h 410 nm
ACN NH +
O
O O
R1 R1CO2H
R1 = carboxylic acid residue
N O
O
O h 410 nm S ACN
+ NH O
O O
R2SO3H R2 = sulfonic acid residue
O R2
b) 19°
a) 130°
Photo irradiation
Chapter-2
Chapter-3
Chapter-4 Chapter-5
