345915-48-2

Upstream product

• 138519-02-5 dimethyl 4,5-bis(methylthio)-1,3-dithiole phosphonate ester 
• 345915-46-0 2,6-bis(2-tercbutyldiphenylsilyloxyethyloxy)-9,10-anthraquinone 
• 84-60-6 anthraflavic acid 
• 58479-61-1 tert-butylchlorodiphenylsilane 
• 500004-01-3 2,6-bis(2-hydroxyethyloxy)-9,10-anthraquinone 
• 139897-19-1 (2-bromoethoxy)(tert-butyl)diphenylsilane 

Relevant academic research and scientific papers

Synthesis and properties of bingel-type methanofullerene - π-extended-TTF diads and triads

Novel C60/π-extended tetrathiafulvalene (exTTF) diads (12a-c) and triads [D2A (14a-c) and DA2 (25, 27a-c)] have been synthesized by the Bingel cyclopropanation reaction of the respective exTTF-containing malonates and [60]fullerene. The reaction of exTTF-bismalonates with C60 affords the respective C60-exTTF diads (26a-c) together with the triad C60-exTTF-C60 (25, 27a-c) and a regioisomeric mixture of bisadducts (28b-c). Theoretical calculations (PM3) predict the favored geometry for triads 14a-c depending upon the orientation (up and down) of the 1,3-dithiole rings in the exTTFs, as well as the more stable regioisomers for the bisadducts 28. Cyclic voltammetry measurements reveal that C60 and exTTF units do not intereact in the ground state. Compounds 26a-c and 27a-c are not electrochemically stable. A photoinduced electron transfer leading to the formation of the radical pair (C60--exTTF?+) has been observed for compounds 14a-c.

Molecular saddles. 7. New 9,10-Bis(1,3-dithiol-2-ylidene)-9,10-dihydroanthracene cyclophanes: Synthesis, redox properties, and x-ray crystal structures of neutral species and a dication salt

We report the synthesis of cyclophanes 18-20 by ester-forming macrocyclization reactions of diols 15 and 16 with 1,4-benzenedicarbonyl chloride. Compounds 18 and 19 display a two-electron, quasireversible oxidation wave in the cyclic voltammogram to yield the dication species at Eoxpa 0.52 and 0.47 V, respectively (vs Ag/AgCl in acetonitrile), whereas the 2 + 2 product 20 undergoes a single four-electron oxidation process at Eoxpa 0.51 V. X-ray crystal structures are reported for compounds 18-20 and the dication salt 182+(I3-)2· (I2)0.5. For comparative purposes, the structures are also reported for the precursor diol 15 and its dication salt 152+(ClO4-)2, which was obtained by electrocrystallization. In the neutral cyclophanes 18-20, the 9,10-bis(1,3-dithiol-2-ylidene)-9, 10-dihydroanthracene moieties adopt a saddle-shaped conformation. The overall measure of folding, the dihedral angle (θ) between the S(1)C(16)C(17)S(2) and S(5)C(21)C(22)S(6) planes, is similar in 15 and 18 (87.6° and 83.7°, respectively) whereas this angle is significantly narrower in 19 (61.1°), illustrating the flexibility of the saddle conformation and its dependence on the packing. Dimeric molecule 20 contains two saddle moieties with very similar conformations, θ = 73.4° and 73.1°. The structures of dication salts 152+(ClO4-)2 and 182+(I3-)2· (I2)0.5 reveal that a dramatic conformational change accompanies oxidation of the donor with the dithiolium rings planar and nearly perpendicular to the mean plane of the anthracene moieties. A notable feature of 182+ is that the bridge enforces a fold of 22° along the C(9)...C(10) vector of the anthracene unit. In 152+ there is no fold about this axis, instead the anthracene moiety is slightly twisted with the two (planar) outer rings forming an angle of 7°.