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. 2016 Nov 28;55(51):15760–15765. doi: 10.1002/anie.201609481

Figure 6.

Figure 6

Phylloxanthobilin Z 1 dimerizes in CHCl3 in a thermoreversible [2+2] photocycloaddition to octapyrrole 2. Comparison of the calculated structures of the preorganized, self‐templating, hydrogen‐bonded, and π‐stacked homodimer (Z1)2 (top left) and 2 (top right) indicates complete retention of the hydrogen‐bonding network. Photolysis of yellow Z 1‐Me in CHCl3 at 0 °C generates 2‐Me (bottom left). Photodimerization is reversed by thermolysis of 2‐Me at room temperature or 50 °C (bottom right).