Synthesis and Electronic Properties of Length-Defined 9,10-Anthrylene–Butadiynylene Oligomers

Abstract

Linear π-conjugated oligomers consisting of anthracene and diacetylene units were readily synthesized by a one-pot process that involved desilylation and oxidative coupling from appropriate building units. We were able to isolate length-defined oligomers ranging from 2-mer to 6-mer as stable and soluble solids. The bathochromic shifts in the UV-vis spectra suggested that the π-conjugation was extended with elongation of the linear chain. Cyclic voltammetric measurements showed characteristic reversible oxidation waves that were dependent on the number of anthracene units.

Diverse Proton-Conducting Nanotubes via a Tandem Macrocyclization and Assembly Strategy

“…This approach yielded structurally and electronically diverse macrocycles using terephthalaldehyde ( PDA ), 2,3,5,6-tetrafluoroterephthalaldehyde ( F 4 –PDA ), , 2,5-dimethoxyterephthalaldehyde ( DiOMe-PDA ), , and 9,10-anthracenedicarboxaldehyde ( 9,10-ADA ) monomers (Schemes S19–22). , Lastly, we prepared a diamond shaped [2 + 2] macrocycle from DAPP and 4,4′-(1,10-phenanthroline-2,9-diyl)­dibenzaldehyde ( PhenDA ) which can chelate metals within the phenanthroline binding pocket (Scheme S23) , The ability to target macrocycles of different sizes, chemical functionalities, and intrinsic properties highlights the modularity of this approach, and its overall utility in constructing precisely functionalized nanostructures.…”

Synthesis and Evaluation of Charge Transport Property of Ethynylene‐Bridged Anthracene Oligomers

“…As seen in diethynylene‐linked anthracene oligomers, the presence of ethynylene units facilitates quenching via nonradiative pathways. [ 11 ]…”

“…While oxidation waves of 3mer and 4mer are relatively broad, differential pulse voltammetry (DPV) clearly showed the oxidation peaks (Figure 3b). Although the result indicates that more anthracene units in the oligomers lead to more susceptible oxidation, [ 11 ] even 4mer showed the suitable HOMO level as a stable compound.…”

“…These results indicate the electronic communication between anthracene units as seen in the similar systems. [ 8,11 ] The estimated HOMO and the lowest unoccupied molecular orbital (LUMO) are summarized in Table 1. The electrochemically determined HOMO–LUMO gaps are in agreement with the optically estimated values (Table S1, Supporting Information).…”

“…In the block crystal, the three anthracene planes are approximately coplanar along the linear molecular axis, while the molecule is slightly S‐shaped as seen in diethynylene‐bridged anthracene trimer (Figure 4d). [ 11 ] Interestingly, the position of TIPS groups was confirmed at one position without the disorder, implying the packing rigidity. The anthracene moiety adopts a face‐to‐face π‐stack structure with a slip‐stacked packing.…”