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The synthesis of [3.3]dithia-bridged cyclophanes  7 ,  9  and  11  incorporating a fused heterocycle, thieno[2,3- b ]thiophene is described. The structures are established by  1 H NMR analysis and, in the case of  11 , also by single crystal X-ray crystallography. Conformational analysis by variable temperature NMR suggests that cyclophanes  7 ,  9  and  11  exhibit conformationally rigid bridges and rings at least up to 130 °C. Energy minimization of  11  revealed   anti   -11  to be the most stable conformation. Although, the computed energy difference between the most stable conformation   anti   -11  and the next higher energy conformation   syn-anti   -11  is only 2.98 kJ/mol, it is intriguing that  11  does not exhibit thia-bridge inversion even at elevated temperatures.

[3.3]Dithia-bridged cyclophanes featuring a thienothiophene ring: synthesis, structures and conformational analysis