Fused ring monomers providing for chemically recyclable polymers
A monomer capable forming a polymer through ring-opening metathesis polymerization and capable of depolymerization thereafter through ring-closing metathesis, wherein the monomer comprises a cycloalkene having a fused ring attached thereto which decreases the ring strain energy to 5.3 kcal/mol or lower as compared to the same cycloalkene without a fused ring having a ring strain energy above 5.3 kcal/mol.
1 . A monomer capable of forming a polymer through ring-opening metathesis polymerization and capable of depolymerization thereafter through ring-closing metathesis, the monomer comprising:
a cycloalkene having a fused ring attached thereto which decreases the ring strain energy to 5.3 kcal/mol or lower as compared to the same cycloalkene without a fused ring having a ring strain energy above 5.3 kcal/mol.
2 . The monomer of claim 1 , wherein the cycloalkene is a 7- to 12-membered cycloalkene.
3 . The monomer of claim 1 , wherein the fused ring is either cis-fused or transfused.
4 . The monomer of claim 2 , wherein the cycloalkene is an 8-membered cycloalkene, cyclooctene.
5 . The monomer of claim 1 , wherein the fused ring is a 3- to 6-membered ring.
6 . The monomer of claim 5 , wherein the fused ring is a 4-membered ring, cyclobutane.
7 . The monomer of claim 5 , wherein the fused ring is a 5-membered ring, cyclopentane.
8 . The monomer of claim 4 , wherein the fused ring is fused at the C5, C6-positions of the cyclooctene.
9 . The monomer of claim 8 , wherein the fused ring is trans-cyclobutane or trans-cyclopentane.
10 . A monomer forming a polymer through ring-opening metathesis polymerization and capable of depolymerization thereafter through ring-closing metathesis, the monomer comprising:
a cycloalkene having a fused ring attached thereto wherein the attachment of the fused ring results in a change of less than 1° of an average difference in dihedral angles from a corresponding acyclic diene of the cycloalkene having a fused ring attached thereto, as measured at the attachment of the fused ring.
11 . The monomer of claim 10 , wherein the cycloalkene is a 7- to 12-membered cycloalkene.
12 . The monomer of claim 10 , wherein the fused ring is either cis-fused or transfused.
13 . The monomer of claim 11 , wherein the cycloalkene is an 8-membered cycloalkene, cyclooctene.
14 . The monomer of claim 10 , wherein the fused ring is a 3- to 6-membered ring.
15 . The monomer of claim 14 , wherein the fused ring is a 4 -membered ring, cyclobutane.
16 . The monomer of claim 14 , wherein the fused ring is a 5 -membered ring, cyclopentane.
17 . The monomer of claim 13 , wherein the fused ring is fused at the C5, C6-positions of the cyclooctene.
18 . The monomer of claim 17 , wherein the fused ring is trans-cyclobutane or trans-cyclopentane.
19 . A method of synthesizing a monomer capable of forming a polymer through ring-opening metathesis polymerization and capable of depolymerization thereafter through ring-closing metathesis, the method comprising:
i. providing a cyclic diene;
ii. performing a photochemical 2+2 cycloaddition with an olefin to the cyclic diene.