Pentaerythritol tetrakis(4-iodo-2,3,5,6-tetrafluorophenyl) ether: a tecton for the self-assembly of double strand 1D infinite chains

The p-iodotetrafluorophenyl motif has been appended to the four alcoholic groups of pentaerythritol to give the corresponding tetraether 1, which works as an effective tecton in halogen bonding based crystal engineering. In fact, in the solution and the solid phases, the halogen bonding drives the self-assembly of this ether with primary, secondary, and tertiary amines as well as with pyridine derivatives. Co-crystals are isolated where I invariably works as a tetradentate halogen bonding donor. Double strand, ID, infinite chains are formed where the nitrogen substituted motifs are pinned in positions that fulfil Schmidt's requirements for solid phase photocycloaddition reactions. Quantitative yields and complete stereoselectivity have been obtained in the cycloaddition reaction. (c) 2004 Elsevier B.V. All rights reserved.