4.8 Article

A Push-Pull Macrocycle With Both Linearly Conjugated and Cross-Conjugated Bridges

Journal

ORGANIC LETTERS
Volume 15, Issue 14, Pages 3762-3765

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ol401697d

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Funding

  1. Air Force Office of Scientific Research [FA9550-10-1-0377]

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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.

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