Design of star-shaped organoiron oligomers with azo dye bridges.

A series of star-shaped macromolecules bearing distinct symmetrical branches with alternating organoiron complexes and azobenzene moieties were synthesized using both convergent and divergent approaches. The various azo dye and organoiron-containing branches were reacted with multifunctional cores via metal-mediated nucleophilic aromatic substitution and ester condensation reactions to afford multi-substituted three- and four-arm star-shaped oligomers. UV–vis spectral studies of complexes 15 and 22 (λ max = 435 and 427 nm, respectively) show bathochromic shifts (λ max = 576 and 558, respectively) at various HCl concentrations indicating their use as potential acid sensors. Cyclic voltammetric studies of the octa-iron oligomer 22 were reversibly reduced at E 1/2 = −1.53 V.Copyright (C) 2012 American Chemical Society (ACS). All Rights Reserved.; Section Code: 41-3; CA Section Cross-references: 29, 76; CODEN: JIOPAY; CAS Registry Numbers: 1253375-71-1P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (G1; design of star-shaped organoiron oligomers with azo dye bridges); 1253375-91-5P Role: PRP (Properties), RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (design of star-shaped organoiron oligomers with azo dye bridges); 1253413-49-8P Role: PRP (Properties), SPN (Synthetic preparation), PREP (Preparation) (design of star-shaped organoiron oligomers with azo dye bridges); 92-50-2 (N-(2-Hydroxyethyl)-N-ethylaniline); 108-73-6 (Phloroglucinol); 139-65-1 (Bis(4-aminophenyl)sulfide); 554-95-0 (1,3,5-Benzenetricarboxylic acid); 1271-42-7 (Ferrocenylcarboxylic acid); 5675-51-4 (1,12-Dodecanediol); 65902-44-5; 364632-70-2; 556104-30-4; 783361-93-3; 851083-21-1; 1253376-24-7 Role: RCT (Reactant), RACT (Reactant or reagent) (design of star-shaped organoiron oligomers with azo dye bridges); 426208-93-7P; 1253375-58-4P; 1253375-85-7P; 1253376-01-0P; 1253376-12-3P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (design of star-shaped organoiron oligomers with azo dye bridges); 1253375-65-3P; 1253375-74-4P; 1253375-79-9P; 1253376-18-9P Role: SPN (Synthetic preparation), PREP (Preparation) (design of star-shaped organoiron oligomers with azo dye bridges)Source type: Electronic(1