A Doubly Bridged Bis(phenylethynyl)benzene: Different from a Twisted Tolan.

The synthesis of a doubly bridged 1,4-bis(phenyl-ethynyl)-benzene is reported. The target displays photophysical properties,  distinctly different from that of its congeners, the singly bridged tolans. Quantum-chemical calculations suggest a lack of planarization of the bridged bis(phenylethynyl)benzene in the first excited state.