87387-08-4

Upstream product

• 87386-97-8 <3.3>Paracyclophan-5,8-dicarbonsaeure-dimethylester 
• 87386-95-6 2,13-Dithia<4.4>paracyclophan-16,19-dicarbonsaeure-dimethylester 
• 87387-09-5 Tricyclo[10.2.2.2^5,8]octadeca-1⁽¹⁵⁾,5⁽¹⁸⁾,6,8⁽¹⁷⁾,12⁽¹⁶⁾,13-hexaene-6,17-dicarbonyl dichloride 
• 74362-77-9 <3.3>Paracyclophan-5,8-dicarbonsaeure 
• 54100-54-8 dimethyl 2,5-bis(bromomethyl)benzene-1,4-dicarboxylate 
• 100-51-6 benzyl alcohol 
• 87386-96-7 2,13-Dithia<4.4>paracyclophan-16,19-dicarbonsaeure-dimethylester-2,2,13,13-tetraoxid 
• 87387-10-8 Tricyclo[10.2.2.2^5,8]octadeca-1⁽¹⁵⁾,5⁽¹⁸⁾,6,8⁽¹⁷⁾,12⁽¹⁶⁾,13-hexaene-6,17-dicarbonyl diazide 

Relevant academic research and scientific papers

Electron Donor-Acceptor Compounds, XXXII. An Electron Donor-Acceptor Paracyclophane with N,N,N',N'-Tetramethyl-p-phenylene-diamine and 7,7,8,8-Tetracyanoquinodimethane Subunits

In an attempt to obtain electron donor-acceptor cyclophanes with a diradical-zwitterionic ground state the paracyclophane 1 was synthesized. 1 contains the combination of the N,N,N',N'-tetramethyl-p-phenylenediamine (TMPD) unit as a strong donor with the tetracyanoquinodimethane (TCNQ) unit as a strong acceptor.The key intermediate for the synthesis of 1, 5,8-bis(methoxycarbonyl)paracyclophane (2), was obtained via the corresponding dithiaparacyclophane and its disulfone.Chloromethylation of 2 yielded 3; via 4 and 5 and subsequent Curtius rearrangement 6 w as obtained which by catalytic hydrogenation and methylation yielded 7.By transformation of the bis(cyanomethyl)-substituted ring of 7 into the TCNQ unit 1 was formed. - In the near infrared the electron spectrum of 1 contains a strong charge transfer absorption the solvent dependence of which was investigated.It is shown from these results as well as from other spectroscopic evidence (IR, ESR) that 1 does not exist in a diradical-zwitterionic ground state. - By X-ray structure analysis of 7 the assignment of the pseudogeminal structure has been proven for 1 and for the intermediates 3 to 7. - For spectroscopic comparison with 1 the TMPD-paracyclophane 8 was prepared starting from 2.