Maleimide copolymers containing azobenzene moieties – synthesis and study of liquid crystalline and optical properties

Abstract

New reactive copolymers have been synthesized by copolymerization of two functional N-substituted-maleimides with styrene.

On the Charge-Transfer Excitations in Azobenzene Maleimide Compounds: A Theoretical Study

“…The eight AB–MI derivatives in the trans form ( E ) and their cis isomers ( Z ) shown in Figure were investigated, and they will be considered for discussion as follows: ( E 1): ( E )-1-(4-(phenyldiazenyl) phenyl)-1 H -pyrrole-2,5-dione; ( Z 1): ( Z )-1-(4-(phenyldiazenyl)­phenyl)-1 H -pyrrole-2,5-dione; ( E 2): ( E )-1,1′-(4-( p -tolyldiazenyl)-1,3-phenylene)-bis-(1 H -pyrrole-2,5-dione); ( Z 2): ( Z )-1,1′-(4-( p -tolyldiazenyl)-1,3-phenylene)-bis-(1 H -pyrrole-2,5-dione); ( E 3): ( E )-1,1′-(4-( o -tolyldiazenyl)-1,3-phenylene)-bis-(1 H -pyrrole-2,5-dione); ( Z 3): ( Z )-1,1′-(4-( o -tolyldiazenyl)-1,3-phenylene)-bis-(1 H -pyrrole-2,5-dione); ( E 4): ( E )-4-(2,5-dioxo-2 H -pyrrol-1­(5 H )-yl)- N -(4-(phenyldiazenyl)­phenyl)­benzamide; and ( Z 4): ( Z )-4-(2,5-dioxo-2 H -pyrrol-1­(5 H )-yl)-(4-(phenyldiazenyl)­phenyl)­benzamide. The preparation and characterization of these AB-MI compounds have been described previously. ,, Spectral properties of the E 4 isomer, including the solvatochromic behavior applying different solvation model parameters, partial atomic charges in the ground and excited states, the molecular electrostatic potential diagrams, and the solute–solvent interactions, have been previously discussed in ref . This study does not, however, contain any calculations or discussion of possible CT effects in the presence of the added MI moieties, which is the focus in this work.…”

“…AB structures, substituted with MI groups, have been investigated because of their ability to exhibit enantiotropic crystalline behavior, to improve the optical properties and the thermal stability of some polymer matrices. , Furthermore, the AB-functionalized poly-(N-substituted MI- alt -styrene) has been used for photostimulated phase separation encapsulation . Other applications of AB–MI systems that have received increasing interest during the last years include photoswitches for visible light control of an ionotropic glutamate receptor, red light photocontrol of conformation of some AB di-MI compounds, and photoswitches designed for glutamate receptor optogenetics …”

“…21 The MI structure can induce a CT interaction which is a key condition for initiation and transfer reactions during polymerization. 22−24 AB structures, substituted with MI groups, have been investigated because of their ability to exhibit enantiotropic crystalline behavior, 25 to improve the optical properties and the thermal stability of some polymer matrices. 26,27 Furthermore, the AB-functionalized poly-(N-substituted MI-altstyrene) has been used for photostimulated phase separation encapsulation.…”

Synthesis and Ozone Degradation of Alternating Copolymers ofN‐Substituted Maleimides with Diene Monomers

“…The produced MAn copolymers are used as functional polymers, such as paints, industrial resins, sizing agents for paper, surface active agents, additives for food, anticancer drugs, and so on . On the other hand, RMI copolymers are used as high‐performance transparent polymer materials for optical devices due to their excellent thermal, optical, and mechanical properties . In contrast to facile copolymerization of MAn and RMIs with olefins, these electron‐accepting monomers predominantly yield Diels–Alder adducts during reactions with 1,3‐dienes, such as butadiene, cyclopentadiene, and furan .…”

“…[7,8] On the other hand, RMI copolymers are used as high-performance transparent polymer materials for optical devices due to their excellent thermal, optical, and mechanical properties. [9][10][11][12][13][14][15][16][17][18] In contrast to facile copolymerization of MAn and RMIs with olefins, these electron-accepting monomers predominantly yield Diels-Alder adducts during reactions with 1,3-dienes, such as butadiene, cyclopentadiene, and furan. [19,20] Previously, we reported that…”