A push–pull macrocycle with both linearly conjugated and cross-conjugated bridges

Wade C. W. Leu and C. Scott Hartley*
Org. Lett. 2013, 15, 3762–3765
[Published version]


A series of shape-persistent macrocycles featuring both m-phenylene and 2,5-thiophene linkers has been synthesized, including an example where they bridge electron-rich (veratrole) and electron-poor (phthalimide) units. Charge transfer in this “push–pull macrocycle” has been investigated by UV–vis and fluorescence spectroscopies and DFT calculations. The effect of pairing structurally distinct conjugated bridges is discussed in the context of acyclic and symmetrical macrocyclic analogs.