A series of dithia[3.3]paracyclophane-fluorene copolymers
1a-c and
3-5 were synthesized bya palladium-catalyzed reaction between 9,9-di-
n-hexylfluorene-2,7-bis(trimethylene boronate) and the correspondingdithiacyclophane precursors. The transannular
![](/images/gifchars/pi.gif)
-
![](/images/gifchars/pi.gif)
interaction in the dithiaparacyclophane modified the electronicand optical properties of the copolymers significantly, resulting in emission red shifts relative to a referencepolymer
2. The observed shift in
1a and
5 was accompanied by enhanced photoluminescence (PL) efficiency,whereas that in
1b,
1c,
3, and
4 experienced a significant to nearly complete fluorescence quenching. The quenchingeffect is likely to involve an electron-transfer process and could be correlated qualitatively to the reduction potentialof the "external" aromatic moiety in the cyclophane unit.