Near-Infrared Absorbing Compounds Based on π-Extended Tetrathiafulvalene Open-Cage Fullerenes

Abstract

Tetrathiafulvalene (TTF) is attached to open-cage fullerenes through a quinoxaline junction. The resulting linear π-conjugation system shows intense absorption in the near-infrared region. A unique o-diaminobenzene-induced furan ring formation process from a conjugated 1,4-dione moiety was observed on the rim of a 18-membered orifice.

Peroxide‐Mediated Selective Cleavage of [60]Fullerene Skeleton Bonds: Towards the Synthesis of Open‐Cage Fulleroid C55O5

“…The isomer 39 was also prepared from 32 in one step, and was shown to be a good sensor for the fluoride ion . The planar tetrathiafulvalene (TTF) π system in 40 is fully conjugated with the curved fullerene π system, and 40 shows intense absorption in the near‐infrared region due to this extended π system. Prior to our work, Xiao et al.…”

Reactions of Diaminonaphthalenes with a Cage‐Opened C60 Derivative

“…Subsequently, they utilized these products as hosts capable of encapsulating molecules such as H 2 O, [4] CO, [5] NH 3 , [6] and CH 4 [7] . In 2014, Gan and co‐workers synthesized related C 60 derivatives with an extended π‐system [2b] by dehydration reactions with aromatic 1,2‐diamines, [8] which exhibited intense absorption in NIR region. Later, they synthesized another cage‐opened system by reactions with aromatic diamine, enabling encapsulation of MeOH, EtOH, LiF, and [BeF] + [9] .…”

π-Extended Open-[70]Fullerenes with a Fused Azaacene

“…For example, in 2004, Iwamatsu and co-workers found a consecutive CC bond scission of open-[60]­fullerenes by a reaction with aromatic diamines, in which the two carbonyl groups remained intact while the diamine was merged with the π-skeleton of the [60]­fullerene cage through a fused pyrazine ring . The related π-extended [60]­fullerenes were, afterward, prepared through a conventional dehydration reaction with aromatic diamines at the iminocyclopentene dione or bis­(imino)­cyclopentenone moiety on open-[60]­fullerenes. Recently, we developed a synthetic method for producing π-extended [60]­fullerenes having a fused imidazole by a reaction using 1,2-diaminoarene with a weak aromaticity, in which characteristic absorption behavior is induced by the effective π-conjugation with the introduced planar π-system .…”