Polymerization of Tricyclononenes

• Published in: Polymer science. Series C 2019-09, Vol.61 (1), p.17-30
• Main Authors: Finkelshtein, E. Sh, Chapala, P. P., Gringolts, M. L., Rogan, Yu. V.
• Format: Article
• Language: English
• Subjects: Addition polymerization; Chemical synthesis; Chemistry; Chemistry and Materials Science; Cyclobutane; Cyclopentadiene; Dienes; Gas membrane separation; Gas separation; Isomerization; Metathesis; Monomers; Organic chemistry; Polymer chemistry; Polymer Sciences; Polymerization; Silicon
• ISSN: 1811-2382; 1555-614X
• DOI: 10.1134/S1811238219010077

The expansion of the range of available and reactive monomers allowing preparation of novel polymeric materials, is an actual task of polymer chemistry. This mini-review is devoted to the polymerization of tricyclo [4.2.1.0 2,5 ]non-7-enes (tricyclononenes) and tricyclo[4.2.1.0 2,5 ]nona-3,7-dienes (tricyclonona-dienes)–norbornene type monomers containing norbornene and cyclobutane or cyclobutene fragments in the molecules. Their synthesis is carried out using available cyclopentadiene or quadricyclane, which is a product of norbornadiene photo-isomerization. The features of ring-opening metathesis and addition polymerization of tricyclononenes with participation of double bond in the norbornene fragment are highlighted. Examples of the polymerization of a wide range of tricyclononenes with F-, Si-, O-, and N-containing substituents have demonstrated that they are noticeably more active monomers than norbornenes with the same substituents. The main successes have been achieved in the synthesis of F- and Si-substituted polytricyclononenes, which are promising materials for lithography and membrane gas separation.