Abstract Azobenzenophanes are fascinating macrocycles, which are of special interest due to their unique photochromic behavior. Cyclotrisazobenzenes 2 (R= H, Br, tBu) were prepared to probe how much strain the photoisomerization of the azobenzene motive can tolerate. The macrocycles were synthesized in an overall yield of 10–20% from ortho- phenylenediamine (6). Solid-state structures of cyclotrisazobenzenes 2a and 2b were ...