A polythioether prepolymer comprising a moiety of Formula: -S-R 1 -[S-A-S-R 1 -] s -S- wherein, s is an integer from 1 to 60; each R 1 is independently selected from C 2-10 alkanediyl, C 6-8 cycloalkanediyl, C 6-10 alkanecycloalkanediyl, and -[(-CHR-) p -X-] q - r -, wherein each R is independently selected from hydrogen and methyl, wherein, each X is independently selected from -O- and -S-; each p is independently an integer from 2 to 6; q is an integer from 1 to 5; and r is an integer from 2 to 10; each A is independently selected from a sulfur-containing moiety of Formula, a moiety of Formula, and a moiety derived from an alkenyl-terminated polyfunctionalizing agent, wherein from 10 mol% to 90 mol% of the A moieties comprise a sulfur-containing moiety of Formula: -(CH 2) 2 -O-(CH 2) n -Y 1 -R 4 -Y 1 - n -O-(CH 2) 2 - -(CH 2) 2 -O-(R 2 -O)m-(CH 2) 2 - wherein, each n is independently an integer from 1 to 4; each Y 1 is independently selected from -O- and -S-; m is an integer from 0 to 50; and each R 2 is independently selected from C 2-6 n-alkanediyl, C 3-6 branched alkanediyl, C 6-8 cycloalkanediyl, C 6-10 alkanecycloalkanediyl, and -[(CH 2) p -X-] q -(CH 2) r -, wherein, each p is independently an integer from 2 to 6; q is an integer from 1 to 5; and r is an integer from 2 to 10; R 4 is selected from C 2-6 n-alkanediyl, C 3-6 branched alkanediyl, C 6-8 cycloalkanediyl, C 6-10 alkanecycloalkanediyl, and -[(CH 2) p -X-] q -(CH 2) r -, wherein, each X is independently selected from -O-, -S-, and -S-S-; each p is an integer from 2 to 6; q is an integer from 1 to 5; and r is an integer from 2 to 10; and at least one Y 1 is -S-, or R 4 is -[(CH 2) p -X-] q -(CH 2) r - and at least one X is selected from -S- and -S-S-, wherein mol% is based on the total moles of A moieties in the prepolymer. s is an integer from 1 to 60; each R 1 is independently selected from C 2-10 alkanediyl, C 6-8 cycloalkanediyl, C 6-10 alkanecycloalkanediyl, and -[(-CHR-) p -X-] q - r -, wherein each R is independently selected from hydrogen and methyl, wherein, each X is independently selected from -O- and -S-; each p is independently an integer from 2 to 6; q is an integer from 1 to 5; and r is an integer from 2 to 10; each n is independently an integer from 1 to 4; each Y 1 is independently selected from -O- and -S-; m is an integer from 0 to 50; and each R 2 is independently selected from C 2-6 n-alkanediyl, C 3-6 branched alkanediyl, C 6-8 cycloalkanediyl, C 6-10 alkanecycloalkanediyl, and -[(CH 2) p -X-] q -(CH 2) r -, wherein, each p is independently an integer from 2 to 6; q is an integer from 1 to 5; and r is an integer from 2 to 10; R 4 is selected from C 2-6 n-alkanediyl, C 3-6 branched alkanediyl, C 6-8 cycloalkanediyl, C 6-10 alkanecycloalkanediyl, and -[(CH 2) p -X-] q -(CH 2) r -, wherein, each X is independently selected from -O-, -S-, and -S-S-; each p is an integer from 2 to 6; q is an integer from 1 to 5; and r is an integer from 2 to 10; and each p is independently an integer from 2 to 6; q is an integer from 1 to 5; and r is an integer from 2 to 10; R 4 is selected from C 2-6 n-alkanediyl, C 3-6 branched alkanediyl, C 6-8 cycloalkanediyl, C 6-10 alkanecycloalkanediyl, and -[(CH 2) p -X-] q -(CH 2) r -, wherein, each X is independently selected from -O-, -S-, and -S-S-; each p is an integer from 2 to 6; q is an integer from 1 to 5; and r is an integer from 2 to 10; and at least one Y 1 is -S-, or R 4 is -[(CH 2) p -X-] q -(CH 2) r - and at least one X is selected from -S- and -S-S-, wherein mol% is based on the total moles of A moieties in the prepolymer.