Unexpected photochemical debenzylation of 2,5-bis(dibenzylamino)-3,6-dichloro-p-benzoquinone

• Two N-benzyl-substituted diaminodichlorobenzoquinones were obtained from the title compound by light irradiation.
• The two derivatives were obtained in approximately 30% yields by Xe-lamp irradiation.
• Crystal structures of the three diaminodichlorobenzoquinone dyes were analyzed.
• Absorption spectra of the three dyes were characterized in the solution and crystalline states.

Studies on the conformational polymorphism of organic dyes with bulky and flexible substituents showed that the benzyl moiety of 2,5-bis(dibenzylamino)-3,6-dichloro-p-benzoquinone can be easily eliminated under ambient light conditions to afford two analogous derivatives, 2,5-bis(benzylamino)-3,6-dichloro-p-benzoquinone and 2-amino-5-benzylamino-3,6-dichloro-p-benzoquinone. Herein, we report the optical properties as well as the molecular and crystal structures of these three diaminodichlorobenzoquinone dyes with the details of their crystallization. The responses of 2,5-bis(dibenzylamino)-3,6-dichloro-p-benzoquinone under irradiation in solution and the crystalline states are reported.

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