Synthesis and photochemistry of two quinoline analogs of the perimidinespirohexadienone family of photochromes

Experimental and computational electrochemistry of quinazolinespirohexadienone molecular switches – differential electrochromic vs photochromic behavior

“…Most surprisingly, when 3b was photolyzed to form 4b in solution under similar conditions to our previous report [21] and then analyzed electrochemically (Fig. 3 and d, dashed green and orange), four reduction (and oxidation) peaks in the region of the LW isomer were observed.…”

“…Due to the saturated spirocyclic carbon insulating the dienone electrophore from the quinoline moiety in the SW form, we expected minimal change in the SW reduction potential relative to the PSHDs, but a significant difference for the completely conjugated LW isomer(s). Previously we reported the detailed synthesis of two novel quinazolinespirohexadienone (QSHD) photochromes 3a , b (Scheme 2) and their photochemical properties as well as a proof of structure for the photochemically generated long-wavelength isomer (pLW) 4a , b (not 5a , b ) [21]. Herein, we report the electrochemistry of these QSHDs.…”

Effects of novel acylhydrazones derived from 4-quinolone on the acetylcholinesterase activity and Aβ42 peptide fibrils formation

“…In a previous work 3 , quinolone 1 was prepared from a Morita-Baylis-Hillman adduct derived from 2-nitrobenzaldehyde. However, the methodology described by Moerdyk et al 14 , proved to be more effective and practical. Thus, 1 was obtained in 82% yield, through a condensation reaction involving diethyl (diethoxymethylene) malonate (DEM) and aniline, as described in the experimental section.…”

Synthesis and Structural Investigation of an “Oxazinoquinolinespirohexadienone” That Only Exists as Its Long-Wavelength Ring-Opened Quinonimine Isomer

“…After the mixture was neutralized, it was vacuum filtered through a medium-porosity frit to isolate 0.026 g (54%) of a black solid. Characterization revealed that both the chlorine atom and the imine had been hydrolyzed, resulting in 7′: 1 Complete spectral data ( 1 H and 13 C NMR, GC−MS, and diamond anvil ATR IR) for compounds 2′b, 4, 5′, 6′, and 7′ (including deuterium exchange NMR experiments for 2′b, 5′, 6′, and 7′, additional 1 H NMR and GC−MS data for compounds 6′ and 7′ formed by hydrolyses of 8 and 3b and 4, respectively, and 50% thermal ellipsoid image of 5′), X-ray crystallography CIF files for 2′b and 5′, and computational data for 1a,b, 2a,b, 2′a,b, 5, 5′, 6, 6′, 7, and 7′. This material is available free of charge via the Internet at http://pubs.acs.org.…”

“…The PSHD family of photochromes offers many properties suitable for gating photoinduced charge transfer (PICT) reactions via photochromic rearrangements as discussed in detail in an earlier manuscript. 1 That manuscript focused on preparing analogues of the PSHDs in which the naphthalene moiety is replaced with a quinoline, resulting in the quinazolinespirohexadienones (QSHDs). These QSHDs are predicted to be more reducible than the parent PSHDs based on a computational method of predicting the ground-state reduction potentials of organic compounds we have reported, 2,3 which we have also confirmed experimentally.…”