This paper describes the fine-tuning of the acidichromic properties of a coumarin-containing colorant 1 by incorporation of electron-donating and electronwithdrawing substituents on the coumarin moiety. Colorant 1 can undergo two distinct and reversible color changes under both strongly acidic and basic conditions, but not in the presence of gaseous ammonia. The results indicated that the bromo-substituted compound 5b changes from red to yellow when exposed to gaseous ammonia, both in solution and on polycarbonate film, suggesting that an electron-withdrawing group at the 7-position of the coumarin moiety made the enolic hydrogen on 5b more susceptible to deprotonation by a base than in the unsubstituted compound 1.

Five 1,1,3-trisubstituted naphtho [2,3-c]pyran-5,10-dione derivatives were designed and synthesized in five steps from 2-acetyl-1,3-indandione. Prepared quinones 6a-e instantly changed from either red or blue to yellow or orange red, when treated with sodium borohydride in methanol. The resulting reduced hydroquinones 9a-e reverted to their original colors within a few minutes after the reducing agent was