Highly Coplanar Very Long Oligo(alkylfuran)s: A Conjugated System with Specific Head-To-Head Defect

Well-defined monodisperse conjugated oligomers, which have planar backbones and are free from the disturbance of substituents, attract broad interest. Herein, we report a series of symmetrical, isomerically pure oligofurans, namely, the 16-mer <b>16F-6C</b>_<b>6</b> together with the related <b><i>n</i>F-</b><b>2</b><b>C</b>_<b>6</b> (<i>n</i> = 4, 6, 8). Through computational studies and detailed spectroscopic and X-ray characterization, for the first time, we show that the planarity of the furan backbone is almost unaffected by the head-to-head defect which is known to cause considerable twists in its oligo- or poly­thiophene analogues. We present that the properties of these rigid oligo­(alkyl­furan)­s are strongly influenced by the conjugation length. As the longest monodisperse α-oligofuran synthesized to date, <b>16F-6C</b>_<b>6</b> was observed to be stable and highly fluorescent. Experimental and computational studies of the redox states of these oligo­(alkyl­furan)­s reveal that <b>16F-6C</b>_<b>6</b> has singlet biradical (polaron-pair) character in the doubly oxidized ground state: the open-shell singlet (⟨<i>S</i>₂⟩ = 0.989) is 3.8 kcal/mol more stable than the closed-shell dication

High Electrical Conductivity in Ni₃(2,3,6,7,10,11-hexaiminotriphenylene)₂, a Semiconducting Metal–Organic Graphene Analogue

Reaction of 2,3,6,7,10,11-hexa­amino­tri­phenyl­ene with Ni²⁺ in aqueous NH₃ solution under aerobic conditions produces Ni₃­(HITP)₂ (HITP = 2,3,6,7,10,11-hexa­imino­tri­phenyl­ene), a new two-dimensional metal–organic framework (MOF). The new material can be isolated as a highly conductive black powder or dark blue-violet films. Two-probe and van der Pauw electrical measurements reveal bulk (pellet) and surface (film) conductivity values of 2 and 40 S·cm^–1, respectively, both records for MOFs and among the best for any coordination polymer

High Electrical Conductivity in Ni₃(2,3,6,7,10,11-hexaiminotriphenylene)₂, a Semiconducting Metal–Organic Graphene Analogue

Reaction of 2,3,6,7,10,11-hexa­amino­tri­phenyl­ene with Ni²⁺ in aqueous NH₃ solution under aerobic conditions produces Ni₃­(HITP)₂ (HITP = 2,3,6,7,10,11-hexa­imino­tri­phenyl­ene), a new two-dimensional metal–organic framework (MOF). The new material can be isolated as a highly conductive black powder or dark blue-violet films. Two-probe and van der Pauw electrical measurements reveal bulk (pellet) and surface (film) conductivity values of 2 and 40 S·cm^–1, respectively, both records for MOFs and among the best for any coordination polymer