- Oxacycle-Fused [1]Benzothieno[3,2-b][1]benzothiophene Derivatives: Synthesis, Electronic Structure, Electrochemical Properties, Ionisation Potential, and Crystal Structure
-
The molecular properties of [1]benzothieno[3,2-b][1]benzothiophene (BTBT) are vulnerable to structural modifications, which in turn are determined by the functionalization of the backbone. Hence versatile synthetic strategies are needed to discover the properties of this molecule. To address this, we have attempted heteroatom (oxygen) functionalization of BTBT by a concise and easily scalable synthesis. Fourfold hydroxy-substituted BTBT is the key intermediate, from which the compounds 2,3,7,8-bis(ethylenedioxy)-[1]benzothieno[3,2-b][1]benzothiophene and 2,3,7,8-bis(methylenedioxy)-[1]benzothieno[3,2-b][1]benzothiophene are synthesized. The difference in ether functionalities on the BTBT scaffold influences the ionisation potential values substantially. The crystal structure reveals the transformation of the herringbone motif in bare BTBT towards π-stacked columns in the newly synthesized derivatives. The results are further justified by the simulated HOMO levels of the model compound.
- Mohankumar, Meera,Chattopadhyay, Basab,Hadji, Rachid,Sanguinet, Lionel,Kennedy, Alan R.,Lemaur, Vincent,Cornil, Jér?me,Fenwick, Oliver,Samorì, Paolo,Geerts, Yves
-
-
Read Online
- Rhodium-catalysed linear-selective alkyne hydroacylation
-
The use of the electron-rich diphosphine ligand, dcpe, allows the efficient and highly linear selective hydroacylative coupling of aldehydes, including aryl examples, with a range of alkynes.
- Poingdestre, Sarah-Jane,Goodacre, Jonathan D.,Weller, Andrew S.,Willis, Michael C.
-
supporting information; experimental part
p. 6354 - 6356
(2012/07/14)
-
- FACILE SYNTHESIS OF ALKYLTHIOBENZALDEHYDES
-
Alkoxyl alkylthiobenzaldehydes can be readily prepared from the corresponding bromobenzaldehydes and the sodium salt of primary mercaptanes in DMF.
- Schwartz, John A.
-
p. 565 - 570
(2007/10/02)
-
- Monomethylthio analogues of 1-(2,4,5-trimethoxyphenyl)-2-aminopropane
-
Regiospecific syntheses of the three monomethylthio analogues of 1-(2,4,5- trimethoxyphenyl)-2-aminopropane are described. The three isomeric amines were evaluated for potential psychotomimetic potency using the rabbit hyperthermia assay. Enantiomeric com
- Jacob III,Anderson III,Meshul,Shulgin,Castagnoli Jr.
-
p. 1235 - 1239
(2007/10/06)
-