2002
DOI: 10.1021/ar010090s
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Classic Annulenes, Nonclassical Applications

Abstract: This Account details the application of [n]annulenes as functional building blocks for electromechanical actuators, double-helical ladder polymers, and protecting groups for supramolecular interactions. Specifically, redox-induced conformational changes occurring in [8]annulenes are utilized as the transducing element in polymeric electromechanical actuators. Conversely, rigid [8]annulenes are utilized as double-helical fragments for the synthesis of double-helical octaaryl macromolecules. Last, Dewar benzenes… Show more

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Cited by 86 publications
(57 citation statements)
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“…617 Synthesis of a poly[tetra(2,3-thienylene)] P4.16 was realized by typical Ni 0 -catalyzed cross-coupling polymerization of halogenated tetramer 4.16, which in turn was prepared effectively from quaterthiophene 4.15 by oxidative coupling in 48% yield (Scheme 4.3). 615,616 The polymer, a poly([8]-annulene), which was soluble in organic solvents due to the butyl side chains, showed electronic properties typical for polythiophenes; a measurement of actuation, however, could not be obtained.…”
Section: Linkages Including -Positions Of Thiophene Units Leading To mentioning
confidence: 99%
“…617 Synthesis of a poly[tetra(2,3-thienylene)] P4.16 was realized by typical Ni 0 -catalyzed cross-coupling polymerization of halogenated tetramer 4.16, which in turn was prepared effectively from quaterthiophene 4.15 by oxidative coupling in 48% yield (Scheme 4.3). 615,616 The polymer, a poly([8]-annulene), which was soluble in organic solvents due to the butyl side chains, showed electronic properties typical for polythiophenes; a measurement of actuation, however, could not be obtained.…”
Section: Linkages Including -Positions Of Thiophene Units Leading To mentioning
confidence: 99%
“…The authors later polymerized compound 108 due to their interest in the development of polymeric electromechanical actuator devices. They hoped to take advantage of the helical conformation of the racemic annulene 108 by promoting redox-induced conformational changes, which could result in the desired expansion and contraction of the polymeric backbone, i.e., molecular actuation [47].…”
Section: Helical Chirality Using Achiral Building Blocksmentioning
confidence: 99%
“…Cycloadditions are among the most efficient reactions in the repertoire of ring-forming procedures for generating increased molecular complexity [1][2][3][4][5][6][7][8][9][10][11][12][13][14]. These reactions are usually accompanied by the formation of carboncarbon bonds and are achieved under photochemical or thermal conditions.…”
Section: Introductionmentioning
confidence: 99%