2015
DOI: 10.1002/anie.201504713
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Synthesis of the Stable Ordered Conjugated Polymer Poly(dibromodiacetylene) from an Explosive Monomer

Abstract: Dibromobutadiyne is an extremely unstable compound that explodes at room temperature, even under inert atmosphere. This instability has limited the studies of dibromobutadiyne almost entirely to spectroscopic characterization. Here we report an approach to control the reactivity of dibromobutadiyne, via topochemical reaction in cocrystals, leading to the ordered polymer poly(dibromodiacetylene), PBDA. At low temperatures (-15 to -18 °C), dibromobutadiyne can form cocrystals with oxalamide host molecules contai… Show more

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Cited by 30 publications
(29 citation statements)
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“…Very recently, Tykwinski and co-workers reported regioselective Diels-Alder reaction of different hexatriynes (14)(15)(16)(17)(18)(19)(20) with tetraphenylcyclopentadienone followed by further CO extrusion (Scheme 2). [60] As a result variety of hexasubstituted benzenes (21)(22)(23)(24)(25)(26)(27)(28) were obtained.…”
Section: Polyynes As Well As Acetylenes May Undergo Different [2+2] Omentioning
confidence: 99%
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“…Very recently, Tykwinski and co-workers reported regioselective Diels-Alder reaction of different hexatriynes (14)(15)(16)(17)(18)(19)(20) with tetraphenylcyclopentadienone followed by further CO extrusion (Scheme 2). [60] As a result variety of hexasubstituted benzenes (21)(22)(23)(24)(25)(26)(27)(28) were obtained.…”
Section: Polyynes As Well As Acetylenes May Undergo Different [2+2] Omentioning
confidence: 99%
“…[138,154] In acetylene chemistry, all transformations among terminal, trialkylsilyl, and 1-haloacetylenes are known. Moreover, it is known that Br(C≡C) 2 Br [20] decomposes in seconds at room temperature in opposite to I(C≡C) 2 I. Scheme 38 shows the transformations among those three types of alkynes and polyynes.…”
Section: Transformations Of 1-halopolyynesmentioning
confidence: 99%
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“…Indeed, these directional intermolecular interactions facilitate the preparation of the desired solid-state motifs and architectures (Gilday et al, 2015;Cavallo et al, 2016;Priimagi et al, 2013;Mukherjee et al, 2014;Shirman et al, 2015;Mukherjee et al, 2017). For example, using HBs and XBs, the specific organization of terminal diacetylenes (Li et al, 2009;Ouyang et al, 2003), bromodiacetylenes (Jin et al, 2015) and iododiacetylenes (Jin et al, 2013;Sun et al, 2006) has been obtained to achieve the solidstate topochemical polymerization of diacetylenes. On the other hand, to the best of our knowledge, no chlorodiacetylene topochemical polymerizations have been reported.…”
Section: Chemical Contextmentioning
confidence: 99%