Synthesis of Anthracene-Stacked Oligomers and Polymer

Abstract

Anthracene-stacked oligomers and a polymer were synthesized using a xanthene skeleton as the scaffold, and their structures and properties were fully characterized. Intramolecular pi-pi stacking of the anthracene rings in the ground state and excited state was observed.

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

“…[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. However, owing to the small size of the π-conjugated moieties and to the bulkiness of the xanthene scaffold, their intermolecular interactions were relatively weak.…”

Naphthalene-based oligothiophene-stacked polymers

“…55 We have recently reported the synthesis of aromatic-ring-layered polymers using xanthene compounds as scaffolds. [40][41][42][43][44][45][46][47] [2.2] Paracyclophane-layered polymers, which mimic multilayered cyclophanes, 56-59 exhibited fluorescence resonance energy transfer from the layered paracyclophanes to the end-capping groups. The use of xanthene as a scaffold enabled us to introduce various aromatic compounds, such as phenylenes, 44 carbazoles, 45 thiophenes 46 and anthracene, 47 into the polymers, with the distance between the layered aromatic units being B4.5 Å .…”

“…Poly(dibenzofulvene)s, 4-11 7,7-diarylnorbornane-containing conjugated polymers, 12,13 cyclophanecontaining polymers and face-to-face ferrocene polymers [36][37][38] have been synthesized, and their optical and electrochemical properties have been studied in detail. Polymers with layered aromatic rings and p-electron systems have also been investigated; [39][40][41][42][43][44][45][46][47][48][49][50][51][52][53] for example, Chen et al 53 recently reported the synthesis and formation of a twodimensional assembly of polymeric ladder phanes containing face-toface p-electron systems. These polymers have potential applications in optoelectronic devices and single-molecular devices such as singlemolecular wires.…”

Synthesis of Aromatic-Ring-Layered Polymers

“…Photoluminescence spectra, quantum efficiencies (ΦPL), and lifetimes (τPL) were determined with an excitation wavelength of 400 nm. www.intechopen.com π-Stacked oligomers 25-27 comprising anthracene as the layered unit and xanthene as the scaffold were synthesized (Morisaki et al, 2010a) by repeated Sonogashira-Hagihara couplings (Figure 16). An anthracene-stacked polymer, P16, was also prepared by the reaction of 6 with 28 and 29 in 59% yield with an M n of 4600, as shown in Scheme 8.…”