Biomaterial Database

Synthesis and Polymerization of an ortho-para-Substituted Tetraalkoxy [2.2]Paracyclophane-1,9-diene. 2022

Arielle Mann, and Marcus Weck

Department of Chemistry and Molecular Design Institute, New York University, New York, New York 10003, United States.

This contribution describes the synthesis of an unsymmetrical substituted tetraalkoxy[2.2]paracyclophane-1,9-diene comprised of an ortho-substituted and a para-substituted dioctyloxybenzene. (Sp)-4,5,12,15-tetraoctyloxy-[2.2]paracyclophane-1,9-diene ((Sp)-pCpd) and (Rp)-4,5,13,16-tetraoctyloxy-[2.2]paracyclophane-1,9-diene ((Rp)-pCpd) are formed as planar chiral enantiomers. Unlike other tetraalkoxy-substituted pCpds that form as diastereomers, both the (Sp)-pCpd and the (Rp)-pCpd can be polymerized via ring-opening metathesis polymerization (ROMP) using Grubbs' third generation initiator (G3) as it is achiral. Living ROMP afford copolymers featuring alternating cis,trans-poly(p-phenylenevinylene)s (PPV)s. The polymers' unique, blue-shifted optical properties are due to the alkoxy-substitution in the polymer's backbone and the resulting materials could be photoisomerized to the all-trans polymer. This strategy affords tetraalkoxy-pCpd monomers in high yields for the polymerization of soluble PPVs with low or narrow dispersities.

UI	MeSH Term	Description	Entries
D011090	Polyenes	Hydrocarbons with more than one double bond. They are a reduced form of POLYYNES.	Cumulenes
D011108	Polymers	Compounds formed by the joining of smaller, usually repeating, units linked by covalent bonds. These compounds often form large macromolecules (e.g., BIOPOLYMERS; PLASTICS).	Polymer
D013237	Stereoisomerism	The phenomenon whereby compounds whose molecules have the same number and kind of atoms and the same atomic arrangement, but differ in their spatial relationships. (From McGraw-Hill Dictionary of Scientific and Technical Terms, 5th ed)	Molecular Stereochemistry,Stereoisomers,Stereochemistry, Molecular,Stereoisomer
D058105	Polymerization	Chemical reaction in which monomeric components are combined to form POLYMERS (e.g., POLYMETHYLMETHACRYLATE).	Polymerizations