The synthesis on a gram-scale and the full characterization of naphtho[1,2-b]thiophene and benzo[1,2-b:6,5-b']dithiophene 4-carboxylate esters bearing 2-octyldodecyl side chains, and their stannylated and brominated derivatives, suitable for their insertion into π-conjugated polymers is described. The fully soluble and processable synthons are obtained through a cascade sequence of reactions, namely direct arylation and cross aldol condensation, which create an effective pathway for the annulation and π-extension of suitable, commercially available reagents. The newly reported synthesis are compared, whenever possible, using ‘green chemistry metrics’ with literature synthesis, showing dramatic improvements.
Scalable Synthesis of Naphthothiophene and Benzodithiophene Scaffolds as π-Conjugated Synthons for Organic Materials
Pasini, Dario
;Nitti, Andrea
;
2019-01-01
Abstract
The synthesis on a gram-scale and the full characterization of naphtho[1,2-b]thiophene and benzo[1,2-b:6,5-b']dithiophene 4-carboxylate esters bearing 2-octyldodecyl side chains, and their stannylated and brominated derivatives, suitable for their insertion into π-conjugated polymers is described. The fully soluble and processable synthons are obtained through a cascade sequence of reactions, namely direct arylation and cross aldol condensation, which create an effective pathway for the annulation and π-extension of suitable, commercially available reagents. The newly reported synthesis are compared, whenever possible, using ‘green chemistry metrics’ with literature synthesis, showing dramatic improvements.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
