Warrener, R.Margetic, D.Sun, G.Russell, R.2008-10-312008-10-312003Australian Journal of Chemistry, 2003; 56(4):263-2670004-94251445-0038http://hdl.handle.net/2440/48129© CSIRO 2003Succinimide-functionalized N,O-, N,C-, and N,N-bridged benzo[2]polynorbornanes (benzosesquinorbornadienes) are reported for the first time and are prepared by the cycloaddition of either five-membered cyclic 1,3-dienes onto N-substituted benzo-7-azanorbornadienomaleimides or N-substituted isoindoles onto the appropriate norbornadienomaleimides. These products contain an end-fused norbornene (or a 7-substituted relative) and have been designed to act as alkene BLOCKs for the production of nano-scaffolds with up to six addressable sites supplied by each norbornene unit. The N-bridges in these BLOCKs (and their coupled products) allow N-substituent mobility by invertomerization of the sp3 nitrogen whereas the N-substituents on the succinimides are attached to an sp2 nitrogen atom and remain static. Preferred invertomer geometry can be determined using molecular modelling.enJournal article002008280610.1071/CH022180001825634000032-s2.0-003756416141890