Synthesis of 3,6-Diaminophthalimides for Ureidophthalimide-Based Foldamers

Abstract

[reaction: see text]. Herein, we report an improved methodology for the synthesis of a variety of 3,6-diaminophthalimides in high yields. This enables decoration of the periphery of foldamers with a wide range of functionalities.

Radical cation formation in characterization of novel C3‐symmetric disks and their precursors by matrix‐assisted laser desorption/ionization time‐of‐flight mass spectrometry

“…The disk-shaped molecules were synthesized via a convergent approach. 1,26,27 First, a trialkoxy amine was incorporated into an oligopeptide fragment. In case an achiral glycine is adjacent to the trialkoxy moiety, the Bocprotected dipeptide was directly linked to the trialkoxyamine using O-(benzotriazol-1-yl)-N,N,N 0 ,N 0 -tetramethyluronium hexafluorophosphate (HBTU) as a coupling agent.…”

Chiralitätsverstärkung in dynamischen supramolekularen Aggregaten

“…Sie verhalten sich in Lösung gewöhnlich wie Polymere mit Zufallsstruktur, aber unter bestimmten Bedingungen können sie bevorzugt eine helikale Orientierung einnehmen und sich in diesem Zustand zu kolumnaren Strukturen stapeln. [124][125][126][127][128][129][130] Moore und Ray wiesen nach, dass achirale m-Phenylenethinylen(m-PPE)-Oligomere (Schema 16 a) links-oder rechtsgängige Helices bilden können (Schema 16 b). [131] Wenn eine chirale Seitenkette vorlag (28 b), war eine bestimmte Helizität bevorzugt, und aus CDMessungen wurde die Bildung einer chiralen kolumnaren Überstruktur abgeleitet.…”

Chiral Poly(ureidophthalimide) Foldamers in Water

“…[29,25] Removal of the acetyl functions to afford the corresponding diamine 1 was achieved by exposure of diamide 11 to 1.5 m aqueous HCl in refluxing dioxane followed by neutralization. Subsequent treatment of diamine 1 with 20 wt % phosgene in toluene afforded diisocyanate 2.…”

“…Recently, we reported a general synthetic strategy towards an array of 3,6-diaminophthalimides, [25] the building blocks for the foldamers. In this way chiral oligo(ethylene oxide) side chains have been incorporated in the foldameric structure enabling a CD study-after isolation of the high molecular weight fraction-of the polymer in aqueous solution.…”