Structure and photoconductive behavior of (E-) and (Z-)-1-cyano-1-carbethoxymethylene acenaphthen-2-one taken by stereoselective synthesis

1-Oxo-1H-phenalene-2,3-dicarbonitrile Heteroaromatic Scaffold: Revised Structure and Mechanistic Studies

“…In contrast with this previous result, all attempts to prepare cyanoester derivative 18 by direct treatment of acenaphthylene-1,2-dione 3 with methyl cyanoacetate failed, and the desired product was isolated in low yields (Scheme ). The targeted compound 18 was then prepared in two steps: first, the known Knoevenagel condensation reaction of dione 3 with methyl cyanoacetate provided the geometric isomers ( E ) and ( Z ) of 1-cyano-1-carbethoxymethylene acenaphthen-2-one 16 and 17 , respectively. Attempts to carry out the second step under standards conditions (K 2 CO 3 in refluxing acetonitrile) were unsuccessful, and only low yields of 18 were obtained, along with unidentified byproducts.…”

“…The mixture of methyl (2 Z )-cyano(2-oxoacenaphtylen-1(2 H )-ylidene)acetate ( 16 ) and methyl (2 E )-cyano(2-oxoacenaphtylen-1(2 H )-ylidene)acetate ( 17 ) was obtained according to the procedure described by Kollia et al To a suspension of these compounds ( 16 and 17 ) (150 mg, 1.0 equiv., 0.57 mmol) in a microwave sealed tube were added acetonitrile (4 mL) and K 2 CO 3 (7.8 mg, 0.1 equiv, 0.05 mmol). The tube was set up in a microwave reactor (Multisynth Milestone), and the following reaction conditions were applied: temperature rampe from 20 to 100 °C over 3 min (power limit of 120 W).…”

Photoconductive properties of a π-conjugated α-cyclodextrin containing [2]rotaxane and its corresponding molecular dumbbell

“…The measurements were performed in a photoelectrochemical cell (PEC) with a three electrode configuration including platinum electrodes as counter and reference-electrodes as described before (graphical abstract). 7,8 The supporting redox active electrolyte was an aqueous solution of Na 2 SO 4 containing equimolar quantities of the redox couple a School of Chemical Engineering, National Technical University of Athens (NTUA), K 4 Fe II (CN) 6 /K 3 Fe III (CN) 6 . Potentials were therefore measured versus K 4 Fe II (CN) 6 /K 3 Fe III (CN) 6 (reference) and are reported versus the normal hydrogen electrode (NHE) through the addition of 360 mV 16 to the measured potential.…”

“…6 It has been known that a variety of organic molecules display photoconductive properties. 7,8 These materials are grouped into several categories on the basis of their chemical structures. The development of an extensive p-conjugated system in the molecule and the incorporation of a nitro (-NO 2 ) and/or an azo (-NQN-) moiety could lead to novel conducting materials.…”