Novel foldamer structural architecture from cofacial aromatic building blocks

Abstract

This communication demonstrates the utility of peri-substituted 1,8-diphenylnaphthalene as an effective building block for the construction of novel conformationally ordered synthetic oligomers displaying cofacial structural features.

π-Conjugated polymer-layered structures: synthesis and self-assembly

“…24,25 Among the different types of linkers, hairpin-shaped rigid linkers can promote the formation of intramolecular π-stacked structures. [26][27][28][29][30] We have recently reported the synthesis of polymers with layered aromatic rings using a xanthene scaffold as a hairpin-shaped linker; these polymers exhibit intramolecular π-stacked structures with multiple aromatic rings stacked along a single polymer chain. [31][32][33][34][35][36] They can be regarded as the assembly of several small π-conjugated units.…”

Synthesis of peri-Diarylated Naphthalimides via Double Decarboxylative Cross-Coupling Reaction

“…4 Despite their potentially useful applications, push-pull naphthalimides bearing aryl groups at both peri positions have been scarcely reported. 5 Compared to similar systems, peridiarylated derivatives have been extensively studied in 1,8diarylnaphthalenes as model systems for - stacking, 6 foldamers, 7 excimer-based OLEDs, 8 chiral fluorescence sensors, 9 and aggregation induced emission enhancement (AIEE) active materials. 10 Herein, we report a facile synthesis of peri-diarylated naphthalimides via a palladium-catalyzed double decarboxylative cross-coupling reaction.…”

“…1 H NMR (400 MHz, CDCl 3 ):  = 8.68 (d, J = 7.6 Hz, 2 H), 7.64 (d,J = 7.6 Hz,2 H),4 H),4 H),4.22 (t,J = 7.5 Hz, 2 H), 1.77-1.70 (m, 2 H), 1.50-1.44 (m, 2 H), 1.00 (t, J = 7.3 Hz, 3 H). 7,130.3,128.0,122.4,114.6 (d,J C,F = 22 Hz),40.4,30.3,20.5,13.9. Fluorescence (CHCl 3 ,  ex = 368 nm):  em = 446 nm.…”

1,8-Bis(4-methoxy-3-nitrophenyl)naphthalene

“…For use of the title compound as a building block for the synthesis of multidentate ligands, see: Sabater et al (2005); Baruah et al (2007); Prabhakaran et al (2009). For the synthesis of the title compound, see: Letsinger et al (1965); Li et al (2005).…”

“…for the synthesis of multidentate ligands (Sabater et al, 2005), foldamer synthesis (Baruah et al, 2007;Prabhakaran et al, 2009) and as a bridging unit in the design of molecules with antiparallel orientation.…”