Abstract
Carbon-rich organic compounds are candidates for use in a wide range of new technologies. Particularly interesting are materials with a framework of pure carbon, namely the allotropes. Much is known about the most common allotropes, diamond (sp3-carbon) and graphite (sp2-carbon), as well as the newer allotropes, fullerenes, nanotubes, and graphene. On the other hand, little is known about the allotrope constructed from sp-hybridized carbon atoms, a material commonly called carbyne. Without a defined sample of carbyne to study, synthetic chemists have attempted to model the properties of carbyne through the formation of defined length oligomers based on a cumulene or polyyne skeleton. Spectroscopic analysis of these series of oligomers by vibrational (IR and Raman), NMR, and UV/Vis spectroscopy has outlined some of the potential properties of carbyne. Likewise, X-ray crystallographic analyses give further clues as to the structure of carbyne. This review will highlight selected synthetic methods for cumulenes and polyynes, and it then summarizes characterization data related to structure and bonding in these molecules.
Keywords
This is a preview of subscription content, log in via an institution.
Buying options
Tax calculation will be finalised at checkout
Purchases are for personal use only
Learn about institutional subscriptionsNotes
- 1.
A practical definition is required to relate the approach of λ max to λ ∞, i.e., when one consider the two quantities to be equal. Meier's suggestion has been adopted here [107]: considering the accuracy of the typical UV/Vis spectrometer (±1 nm), λ max for carbyne is defined by fulfillment of the relationship λ ∞ – λ (n) ≤ 1 nm. Thus, in the present case, this is true at 485 nm (i.e., 486–485 nm ≤ 1 nm).
- 2.
For non-centrosymmetric structures, the BLA was calculated using the average of positionally equivalent bonds.
References
Diederich F, Rubin Y (1992) Synthetic approaches toward molecular and polymeric carbon allotropes. Angew Chem Int Ed 31(9):1101–1123. doi:10.1002/anie.199211013
He GS, Tan L-S, Zheng Q, Prasad PN (2008) Multiphoton absorbing materials: molecular designs, characterizations, and applications. Chem Rev 108(4):1245–1330. doi:10.1021/cr050054x
Murphy AR, Frechet JMJ (2007) Organic semiconducting oligomers for use in thin film transistors. Chem Rev 107(4):1066–1096. doi:10.1021/cr0501386
Hoeben FJM, Jonkheijm P, Meijer EW, Schenning APHJ (2005) About supramolecular assemblies of π-conjugated systems. Chem Rev 105(4):1491–1546. doi:10.1021/cr030070z
Anthony JE (2006) Functionalized acenes and heteroacenes for organic electronics. Chem Rev 106(12):5028–5048. doi:10.1021/cr050966z
Diederich F, Stang PJ, Tykwinski RR (eds) (2005) Acetylene chemistry: chemistry, biology, and material science. Wiley-VCH, Weinheim
Haley MM, Tykwinski RR (eds) (2006) Carbon-rich compounds: molecules to materials. Wiley-VCH, Weinheim
Hoheisel TN, Schrettl S, Szilluweit R, Frauenrath H (2010) Nanostructured carbonaceous materials from molecular precursors. Angew Chem Int Ed 49(37):6496–6515. doi:10.1002/anie.200907180
Falcao EHL, Wudl F (2007) Carbon allotropes: beyond graphite and diamond. J Chem Technol Biotechnol 82(6):524–531. doi:10.1002/jctb.1693
Kelly B (1981) Physics of graphite. Applied Science Publishers, London
Kirk R, Othmer D, Grayson M, Eckroth D (eds) (1978) Kirk-Othmer encyclopedia of chemical technology, vol 4. Wiley, New York
Chalifoux WA, Tykwinski RR (2006) Polyyne synthesis using carbene/carbenoid rearrangements. Chem Rec 6(4):169–182. doi:10.1002/tcr.20081
Tobe Y, Wakabayashi T (2005) Carbon-rich compounds: acetylene-based carbon allotropes. In: Diederich F, Stang PJ, Tykwinski RR (eds) Acetylene chemistry: chemistry, biology, and material science. Wiley-VCH, Weinheim. doi:10.1002/3527605487.ch9
Chalifoux WA, Tykwinski RR (2009) Synthesis of extended polyynes: toward carbyne. CR Chim 12(3–4):341–358. doi:10.1016/j.crci.2008.10.004
Haley MM (2010) Carbon allotropes on the road to carbyne. Nature Chem 2(11):912–913. doi:10.1038/nchem.884
Cataldo F (1997) A study on the structure and electrical properties of the fourth carbon allotrope: carbyne. Polym Int 44(2):191–200. doi:10.1002/(sici)1097-0126(199710)44:2< 191::aid-pi842>3.0.co;2-y
Cataldo F (ed) (2006) Polyynes: synthesis, properties, and applications. Taylor and Francis, Boca Raton
Kudryavtsev YP, Evsyukov SE, Gusevca M, Babaev C, Khvistov C (1997). In: Thrower PA (ed) Chemistry and physics of carbon, vol 25. Marcel Dekker, New York, pp 1–99
Smith PPK, Buseck PR (1982) Carbyne forms of carbon: do they exist? Science (Washington) 216(4549):984–986. doi:10.1126/science.216.4549.984
Bunz UHF (1996) Organometallic “'carbon chains”': they just keep getting longer! Angew Chem Int Ed 35(9):969–971. doi:10.1002/anie.199609691
Kudryavtsev YP, Heimann RB, Evsyukov SE (1996) Carbynes: advances in the field of linear carbon chain compounds. J Mater Sci 31(21):5557–5571. doi:10.1007/BF01160799
Kuhn R, Wallenfels K (1938) Über Kumulene I. Synthese von Tetraphenyl-hexapentaen und Di-biphenylen-hexapentaen. Chem Ber 71(4):783–790. doi:10.1002/cber.19380710416
Kuhn R, Wallenfels K (1938) Über Kumulene II. Eine wesentliche Verbesserung des Darstellungs-Verfahrens. Chem Ber 71(7):1510–1512. doi:10.1002/cber.19380710725
Kuhn R, Platzer G (1940) Über Kumulene III. Chem Ber 73(12):1410–1417
Kuhn R, Zahn H (1951) Über Kumulene IV. Oktaheptaene. Chem Ber 84(5–6):566–570. doi:10.1002/cber.19510840526
Kuhn R, Krauch H (1955) Über Kumulene VIII. Reduktion von Acetylen-, Diacetylen- und Triacetylen-glykolen mit Zinn-(II)-chlorid; Kumulene mit nur zwei aromatischen Substituenten. Chem Ber 88(3):309–315. doi:10.1002/cber.19550880302
Kuhn R, Blum D (1959) Über Kumulene X. cis-trans-Isomerie bei Dinitro-tetraphenyl-kumulenen. Chem Ber 92(7):1483–1500. doi:10.1002/cber.19590920702
Bohlmann F, Kieslich K (1955) Konstitution und Lichtabsorption, VII. Mitteil.: Über den Einfluß der Phenylchromophore auf die Lichtabsorption der Kumulene. Chem Ber 88(8):1211–1218. doi:10.1002/cber.19550880811
Bohlmann F, Kieslich K (1954) Polyacetylene, VI. Mitteil.: Umwandlung von Polyinen in Kumulene. Chem Ber 87(9):1363–1372. doi:10.1002/cber.19540870926
Bohlmann F, Kieslich K (1957) Untersuchungen in der Kumulen-Reihe. Abh braunschweig wiss Ges 9:147–166
Bohlmann F (1953) Die Polyine. Angew Chem 65(15):385–389. doi:10.1002/ange.1953 0651502
Jones ERH (1960) Pedler lecture. Polyacetylenes. Proc Chem Soc 6:199–210
Jones ERH, Whiting MC, Armitage JB, Cook CL, Entwistle N (1951) Synthesis of polyacetylenic compounds. Nature (London) 168(4282):900–903. doi:10.1038/168900a0
Cook CL, Jones ERH, Whiting MC (1952) Researches on acetylenic compounds. Part XXXIX. General routes to aliphatic polyacetylenic hydrocarbons and glycols. J Chem Soc 2883–2891. doi:10.1039/JR9520002883
Bohlmann F (1951) Konstitution und Lichtabsorption, III. Mitteil.: Polyacetylenverbindungen. Chem Ber 84(9):785–794. doi:10.1002/cber.19510840902
Hunsmann W (1950) Nachweis und Synthese des Triacetylens. Chem Ber 83(3):213–217. doi:10.1002/cber.19500830302
Schlubach HH, Franzen V (1951) Über Polyacetylene III: Über das Diphenyl-pentaacetylen und das Monophenyl-diacetylen. Justus Liebigs Ann Chem 573(1):105–109. doi:10.1002/jlac.19515730111
Schlubach HH, Wolf V (1950) Über Polyacetylene. Justus Liebigs Ann Chem 568(2):141–159. doi:10.1002/jlac.19505680206
Nakagawa M, Akiyama S, Nakasuji K, Nishimoto K (1971) Novel linear relation in the electronic spectra of α, ω-diarylpolyynes. Tetrahedron 27(22):5401–5418. doi:10.1016/S0040-4020(01)91706-5
Viehe HG (ed) (1969) Chemistry of acetylenes. Marcel Dekker, New York
Johnson TR, Walton DRM (1972) Silylation as a protective method in acetylene chemistry. Tetrahedron 28(20):5221–5236. doi:10.1016/S0040-4020(01)88941-9
Eastmond R, Johnson TR, Walton DRM (1973) Base-catalyzed cleavage of silyl-substituted polyynes. Attenuation of hydrocarbon acidity and transmission of substituent electrical effects in long-chain conjugated polyacetylenes. J Organomet Chem 50(1):87–92. doi:10.1016/S0022-328X(00)95093-9
Eastmond R, Johnson TR, Walton DRM (1972) Silylation as a protective method for terminal alkynes. Tetrahedron 28(17):4601–4616. doi:10.1016/0040-4020(72)80041-3
Szafert S, Gladysz JA (2003) Carbon in one dimension: structural analysis of the higher conjugated polyynes. Chem Rev 103(11):4175–4205. doi:10.1021/cr030041o
Szafert S, Gladysz JA (2006) Update 1 of: carbon in one dimension: structural analysis of the higher conjugated polyynes. Chem Rev 106(11):PR1–PR33. doi:10.1021/cr068016g
Zheng Q, Bohling JC, Peters TB, Frisch AC, Hampel F, Gladysz JA (2006) A synthetic breakthrough into an unanticipated stability regime: a series of isolable complexes in which C6, C8, C10, C12, C16, C20, C24, and C28 polyynediyl chains span two platinum atoms. Chem Eur J 12(25):6486–6505. doi:10.1002/chem.200600615
Long NJ, Williams CK (2003) Metal alkynyl σ complexes: synthesis and materials. Angew Chem Int Ed 42(23):2586–2617. doi:10.1002/anie.200200537
Stahl J, Mohr W, de Quadras L, Peters TB, Bohling JC, Martin-Alvarez JM, Owen GR, Hampel F, Gladysz JA (2007) sp Carbon chains surrounded by sp3 carbon double helices: coordination-driven self-assembly of wirelike Pt(C≡C) n Pt moieties that are spanned by two P(CH2) m P linkages. J Am Chem Soc 129(26):8282–8295. doi:10.1021/ja0716103
de Quadras L, Bauer EB, Mohr W, Bohling JC, Peters TB, Martin-Alvarez JM, Hampel F, Gladysz JA (2007) sp Carbon chains surrounded by sp3 carbon double helices: directed syntheses of wirelike Pt(C≡C) n Pt moieties that are spanned by two P(CH2) m P linkages via alkene metathesis. J Am Chem Soc 129(26):8296–8309. doi:10.1021/ja071612n
Suzuki N, Hashizume D, Yoshida H, Tezuka M, Ida K, Nagashima S, Chihara T (2009) Reversible haptotropic shift in zirconocene-hexapentaene complexes. J Am Chem Soc 131(6):2050–2051. doi:10.1021/ja8077472
King RB, Harmon CA (1975) Organometallic chemistry of transition metals XXX. Reactions of tetraalkylhexapentaenes with iron carbonyls. J Organomet Chem 88(1):93–100. doi:10.1016/S0022-328X(00)89333-X
Bildstein B (2000) Cationic and neutral cumulene sp-carbon chains with ferrocenyl termini. Coord Chem Rev 206–207:369–394. doi:10.1016/S0010-8545(00)00248-4
Skibar W, Kopacka H, Wurst K, Salzmann C, Ongania KH, de Biani FF, Zanello P, Bildstein B (2004) α, ω-Diferrocenyl cumulene molecular wires. Synthesis, spectroscopy, structure, and electrochemistry. Organometallics 23(5):1024–1041. doi:10.1021/om034233l
Bildstein B, Skibar W, Schweiger M, Kopacka H, Wurst K (2001) In situ synthesis of the first C7 cumulene (Fc)2C=C=C=C=C=C=C(Fc)2 via deprotonation of its conjugate acid [(Fc)2C7H(Fc)2]+BF4 - (Fc = ferrocenyl). J Organomet Chem 622(1–2):135–142. doi:10.1016/S0022-328X(00)00882-2
Nakamura A (1965) The interaction of cumulene systems with organometallic π-complexes. III. Iron carbonyl complexes of hexapentaene and of tetra- and dimethylbutatriene. Bull Chem Soc Jpn 38(11):1868–1873. doi:10.1246/bcsj.38.1868
Werner H, Wiedemann R, Mahr N, Steinert P, Wolf J (1996) Coordination and coupling of OH-functionalized C2 units at a single metal center: the synthesis of alkynyl(vinylidene), alkynyl(enyne), bis(alkynyl)hydrido, enynyl, and hexapentaene rhodium complexes from propargylic alcohols as precursors. Chem Eur J 2(5):561–569. doi:10.1002/chem.19960020516
Song LS, Arif AM, Stang PJ (1990) Cumulenes as ligands. IV. Rhodium and platinum complexes of tetraphenylhexapentaene. X-ray crystal structure of bis(triphenylphosphine)chloro(tetraphenylhexapentaene)rhodium. J Organomet Chem 395(2):219–226. doi:10.1016/0022-328X(90)85279-8
Fischer H (1964) Cumulenes. In: Patai S (ed) The chemistry of alkenes. Wiley, New York, pp 1025–1159
Ogasawara M (2008) Cumulenes and allenes. In: Krause N (ed) Science of synthesis, vol 44. Georg Thieme Verlag, Stuttgart, pp 9–70
Ried W, Schlegelmilch W, Piesch S (1963) Äthinierungsreaktionen, XX. Über Alkindiole und Kumulene. Chem Ber 96(5):1221–1228. doi:10.1002/cber.19630960508
Dupont G (1913) Recherches sur les γ-glycols acétyléniques et sur les cétohydrofuranes qui en dérivent. Ann Chim Phys 8:485–587
Bergmann E, Hoffmann H, Winter D (1933) Beobachtungen auf dem Gebiet des Fluorens. Chem Ber 66(1):46–54. doi:10.1002/cber.19330660110
Salkind J, Kruglow A (1928) Einwirkung von Jodwasserstoff auf Tetraphenyl-butindiol. Chem Ber 61(10):2306–2312. doi:10.1002/cber.19280611014
Fischer H, Hell WD (1967) UV-Absorption von α, α, ω, ω-Tetraphenylkumulenen mit coplanaren Phenylringen. Angew Chem 79(21):931–932. doi:10.1002/ange.19670792104
Siemsen P, Livingston RC, Diederich F (2000) Acetylenic coupling: a powerful tool in molecular construction. Angew Chem Int Ed 39(15):2632–2657. doi:10.1002/1521-3773(20000804)39:15<2632::AID-ANIE2632>3.0.CO;2-F
Bohlmann F (1953) Polyacetylene, IV. Mitteil.: Darstellung Von Di-tert.-butyl-polyacetylenen. Chem Ber 86(5):657–667. doi:10.1002/cber.19530860519
Jones ERH, Lee HH, Whiting MC (1960) Researches on acetylenic compounds. Part LXIV. The preparation of conjugated octa- and deca-acetylenic compounds. J Chem Soc 3483–3489. doi:10.1039/JR9600003483
Gibtner T, Hampel F, Gisselbrecht JP, Hirsch A (2002) End-cap stabilized oligoynes: model compounds for the linear sp carbon allotrope carbyne. Chem Eur J 8(2):408–432. doi:10.1002/1521-3765(20020118)8:2<408::AID-CHEM408>3.0.CO;2-L
Klinger C, Vostrowsky O, Hirsch A (2006) Synthesis of alkylene-bridged diphenyl-oligoynes. Eur J Org Chem 6:1508–1524. doi:10.1002/ejoc.200500851
Krätschmer W, Lamb LD, Fostiropoulos K, Huffman DR (1990) Solid C60: a new form of carbon. Nature (London) 347(6291):354–358. doi:10.1038/347354a0
Grösser T, Hirsch A (1993) Dicyanopolyynes: formation of new rod-shaped molecules in a carbon plasma. Angew Chem Int Ed Engl 32(9):1340–1342. doi:10.1002/anie.199313401
Schermann G, Grösser T, Hampel F, Hirsch A (1997) Dicyanopolyynes: a homologous series of end-capped linear sp carbon. Chem Eur J 3(7):1105–1112. doi:10.1002/chem.19970030718
Fritsch P (1894) Ueber die Darstellung von Diphenylacetaldehyd und eine neue Synthese von Tolanderivaten. Justus Liebigs Ann Chem 279(3):319–323. doi:10.1002/jlac.18942790310
Buttenberg WP (1894) Kondensation des Dichloracetals mit Phenol und Toluol. Justus Liebigs Ann Chem 279(3):324–337. doi:10.1002/jlac.18942790311
Wiechell H (1894) Kondensation des Dichloracetals mit Anisol und Phenetol. Justus Liebigs Ann Chem 279(3):337–344. doi:10.1002/jlac.18942790312
Eisler S, Slepkov AD, Elliott E, Luu T, McDonald R, Hegmann FA, Tykwinski RR (2005) Polyynes as a model for carbyne: synthesis, physical properties, and nonlinear optical response. J Am Chem Soc 127(8):2666–2676. doi:10.1021/ja044526l
Chalifoux WA, McDonald R, Ferguson MJ, Tykwinski RR (2009) tert-Butyl-end-capped polyynes: crystallographic evidence of reduced bond-length alternation. Angew Chem Int Ed 48(42):7915–7919. doi:10.1002/anie.200902760
Lucotti A, Tommasini M, Fazzi D, Del Zoppo M, Chalifoux WA, Ferguson MJ, Zerbi G, Tykwinski RR (2009) Evidence for solution-state nonlinearity of sp-carbon chains based on IR and Raman spectroscopy: violation of mutual exclusion. J Am Chem Soc 131(12):4239–4244. doi:10.1021/ja078198b
Luu T, Elliott E, Slepkov AD, Eisler S, McDonald R, Hegmann FA, Tykwinski RR (2005) Synthesis, structure, and nonlinear optical properties of diarylpolyynes. Org Lett 7(1):51–54. doi:10.1021/ol047931q
Kendall J, McDonald R, Ferguson MJ, Tykwinski RR (2008) Synthesis and solid-state structure of perfluorophenyl end-capped polyynes. Org Lett 10(11):2163–2166
Tykwinski RR, Kendall J, McDonald R (2009) Pentafluorophenyl end-capped polyynes as supramolecular building blocks. Synlett 13:2068–2075. doi:10.1055/s-0029-1217706
Eisler S, Tykwinski RR (2000) Migrating alkynes in vinylidene carbenoids: an unprecedented route to polyynes. J Am Chem Soc 122(43):10736–10737. doi:10.1021/ja005557t
Jahnke E, Tykwinski RR (2010) The Fritsch-Buttenberg-Wiechell rearrangement: modern applications for an old reaction. Chem Commun 46(19):3235–3249. doi:10.1039/c003170d
Eisler S, Tykwinski RR (2005) Polyynes via alkylidene carbenes and carbenoids. In: Diederich F, Stang PJ, Tykwinski RR (eds) Acetylene chemistry. Wiley-VCH Weinheim, pp 259–302. doi:10.1002/3527605487.ch7
Bruce MI, Smith ME, Zaitseva NN, Skelton BW, White AH (2003) A new approach to the synthesis of carbon chains capped by metal clusters. J Organomet Chem 670(1–2):170–177. doi:10.1016/s0022-328x(02)02186-1
Antonova AB, Bruce MI, Ellis BG, Gaudio M, Humphrey PA, Jevric M, Melino G, Nicholson BK, Perkins GJ, Skelton BW, Stapleton B, White AH, Zaitseva NN (2004) A novel methodology for the synthesis of complexes containing long carbon chains linking metal centres: molecular structures of {Ru(dppe)Cp*}2(μ-C14) and {Co3(μ-dppm)(CO)7}2(μ3:μ3-C16). Chem Commun 8:960–961. doi:10.1039/b315854n
Bruce MI, Zaitseva NN, Nicholson BK, Skelton BW, White AH (2008) Syntheses and molecular structures of some compounds containing many-atom chains end-capped by tricobalt carbonyl clusters. J Organomet Chem 693(17):2887–2897. doi:10.1016/j.jorganchem.2008.06.007; erratum (2009) J Organomet Chem 694(3):478. doi: 10.1016/j.jorganchem.2008.11.007
Bruce MI, Nicholson BK, Zaitseva NN (2009) Two complexes containing 19-atom chains linking metal centres. CR Chim 12(12):1280–1286. doi:10.1016/j.crci.2009.06.002
Chalifoux WA, Tykwinski RR (2010) Synthesis of polyynes to model the sp-carbon allotrope carbyne. Nature Chem 2(11):967–971. doi:10.1038/nchem.828
Müllen K, Wegner G (eds) (1998) Electronic materials – the oligomer approach. Wiley-VCH, Weinheim
Martin RE, Diederich F (1999) Linear monodisperse π-conjugated oligomers: model compounds for polymers and more. Angew Chem Int Ed 38(10):1350–1377. doi:10.1002/(SICI)1521-3773(19990517)38:10<1350::AID-ANIE1350>3.0.CO;2-6
Kuhn R, Fischer H (1959) Über Kumulene. XI. Bis-butatriene und unsymmetrische Butatriene. Chem Ber 92(8):1849–1857. doi:10.1002/cber.19590920817
Otting W (1954) Über Kumulene VII: Die Ultrarotspektren einiger Kumulene und Acetylenglykole. Chem Ber 87(4):611–624. doi:10.1002/cber.19540870427
Innocenti F, Milani A, Castiglioni C (2010) Can Raman spectroscopy detect cumulenic structures of linear carbon chains? J Raman Spectrosc 41(2):226–236. doi:10.1002/jrs.2413
Kuwatani Y, Yamamoto G, Oda M, Iyoda M (2005) Nickel-catalyzed dimerization of [5]cumulenes (hexapentaenes). Bull Chem Soc Jpn 78(12):2188–2208. doi:10.1246/bcsj.78.2188
House HO, Umen MJ (1973) The chemistry of carbanions. XXV. The reaction of various organocopper reagents with α, β-unsaturated carbonyl compounds. J Org Chem 38(22):3893–3901. doi:10.1021/jo00962a016
Armitage JB, Entwistle N, Jones ERH, Whiting MC (1954) Researches on acetylenic compounds. Part XLI. The synthesis of diphenylpolyacetylenes. J Chem Soc 147–154. doi:10.1039/JR9540000147
Rubin Y, Lin SS, Knobler CB, Anthony J, Boldi AM, Diederich F (1991) Solution-spray flash vacuum pyrolysis: a new method for synthesis of linear poliynes with odd numbers of CC bonds from substituted 3,4-dialkynyl-3-cyclobutene-1,2-diones. J Am Chem Soc 113(18):6943–6949. doi:10.1021/ja00018a035
Jones AV (1952) Infra-Red and Raman spectra of diacetylene. P Roy Soc Lond A Mat 211(1105):285–295. doi:10.1098/rspa.1952.0040
Kloster-Jensen E (1972) Preparation of pure triacetylene, tetraacetylene, and pentaacetylene and investigation of their electronic spectra. Angew Chem Int Ed 11(5):438–439. doi:10.1002/anie.197204381
Shindo F, Benilan Y, Chaquin P, Guillemin JC, Jolly A, Raulin F (2001) IR spectrum of C8H2: integrated band intensities and some observational implications. J Mol Spectrosc 210(2):191–195. doi:10.1006/jmsp.2001.8459
Wakabayashi T, Tabata H, Doi T, Nagayama H, Okuda K, Umeda R, Hisaki I, Sonoda M, Tobo Y, Minematsu T, Hashimoto K, Hayashi S (2007) Resonance Raman spectra of polyyne molecules C10H2 and C12H2 in solution. Chem Phys Lett 433(4–6):296–300. doi:10.1016/j.cplett.2006.11.077
Brand K, Busse-Sundermann A (1950) Tetra- [2.4-xylyl]-butatrien und 1.1.4.4-Tetra-[2.4-xylyl]-butin-(2); XVI. Mitteil. über Reduktion organischer Halogenverbindungen und Verbindungen der Tetraarylbutanreihe. Chem Ber 83(1):119–128. doi:10.1002/cber.19500830122
Jousselme B, Blanchard P, Frere P, Roncali J (2000) Enhancement of the π-electron delocalization and fluorescence efficiency of 1,6-diphenyl-1,3,5-hexatriene by covalent rigidification. Tetrahedron Lett 41(26):5057–5061. doi:10.1016/S0040-4039(00)00792-9
Tykwinski RR, Chalifoux W, Eisler S, Lucotti A, Tommasini M, Fazzi D, Del Zoppo M, Zerbi G (2010) Toward carbyne: synthesis and stability of really long polyynes. Pure Appl Chem 82(4):891–904. doi:10.1351/pac-con-09-09-04
Waugh F, Walton DRM (1972) Silylation as a protective method for terminal alkynes in organometallic synthesis. Preparation of 1,4-diethynyltetrafluorobenzene and (pentafluorophenyl)acetylene. J Organomet Chem 39(2):275–278. doi:10.1016/S0022-328X(00)80451-9
Meier H, Stalmach U, Kolshorn H (1997) Effective conjugation length and UV/Vis spectra of oligomers. Acta Polymer 48(9):379–384. doi:10.1002/actp.1997.010480905
Hoffmann R (1987) How chemistry and physics meet in the solid state. Angew Chem Int Ed Engl 26(9):846–878. doi:10.1002/anie.198708461
Kertesz M, Choi CH, Yang S (2005) Conjugated polymers and aromaticity. Chem Rev 105(10):3448–3481. doi:10.1021/cr990357p
Milani A, Tommasini M, Zerbi G (2009) Connection among Raman wavenumbers, bond length alternation and energy gap in polyynes. J Raman Spectrosc 40(12):1931–1934. doi:10.1002/jrs.2342
Zeinalipour-Yazdi CD, Pullman DP (2008) Quantitative structure−property relationships for longitudinal, transverse, and molecular static polarizabilities in polyynes. J Phys Chem B 112(25):7377–7386. doi:10.1021/jp800302s
Yang S, Kertesz M (2006) Bond length alternation and energy band gap of polyyne. J Phys Chem A 110(31):9771–9774. doi:10.1021/jp062701+
Yang S, Kertesz M, Zolyomi V, Kürti J (2007) Application of a novel linear/exponential hybrid force field scaling scheme to the longitudinal Raman active mode of polyyne. J Phys Chem A 111(12):2434–2441. doi:10.1021/jp067866x
Peach MJG, Tellgren EI, Salek P, Helgaker T, Tozer DJ (2007) Structural and electronic properties of polyacetylene and polyyne from hybrid and coulomb-attenuated density functionals. J Phys Chem A 111(46):11930–11935. doi:10.1021/jp0754839
Based on a search of the CCDC, 18 September 2012 (CSD version 5.33, November 11)
Berkovitch-Yellin Z, Leiserowitz L (1977) Electron density distribution in cumulenes: an X-ray study of tetraphenylbutatriene at 20°C and −160°C. Acta Crystallogr Sect B 33(12):3657–3669. doi:10.1107/S0567740877011819
Irngartinger H, Götzmann W (1986) Structure determinations of pentatetraenes−comparison of the structures of cumulenes. Angew Chem Int Ed Engl 25(4):340–342. doi:10.1002/anie.198603401
Woolfson MM (1953) The structure of 1:1:6:6 tetraphenylhexapentaene. Acta Cryst 6(11–12):838–841. doi:10.1107/S0365110X53002465
Suzuki N, Hashizume D, Chihara T (2007) 1,1,6,6-Tetrakis(4-ethylphenyl)-1,2,3,4,5-hexapentaene. Acta Crystallogr Sect E 63(8):o3436. doi:10.1107/s1600536807032576
Irngartinger H, Jager HU (1976) Structure and density distribution of bonding electrons of cumulenes. Angew Chem Int Ed Engl 15(9):562–563. doi:10.1002/anie.197605621
Qi H, Gupta A, Noll BC, Snider GL, Lu Y, Lent C, Fehlner TP (2005) Dependence of field switched ordered arrays of dinuclear mixed-valence complexes on the distance between the redox centers and the size of the counterions. J Am Chem Soc 127(43):15218–15227. doi:10.1021/ja054508j
Zhang C, Cao Z, Wu H, Zhang Q (2004) Linear and nonlinear feature of electronic excitation energy in carbon chains HC2n+1H and HC2n H. Int J Quant Chem 98(3):299–308. doi:10.1002/qua.20023
Weimer M, Hieringer W, Della Sala F, Görling A (2005) Electronic and optical properties of functionalized carbon chains with the localized Hartree–Fock and conventional Kohn–Sham methods. Chem Phys 309(1):77–87. doi:10.1016/j.chemphys.2004.05.026
Scemama A, Chaquin P, Gazeau MC, Benilan Y (2002) Theoretical study of the structure and properties of polyynes and monocyano- and dicyanopolyynes: predictions for long chain compounds. J Phys Chem A 106(15):3828–3837. doi:10.1021/jp013043q
Horny L, Petraco NDK, Pak C, Schaefer HF (2002) What is the nature of polyacetylene neutral and anionic chains HC2n H and HC2n H− (n = 6−12) that have recently been observed? J Am Chem Soc 124(20):5861–5864. doi:10.1021/ja012014q
Constable EC, Gusmeroli D, Housecroft CE, Neuburger M, Schaffner S (2006) 1,4-Bis(triisopropylsilyl)buta-1,3-diyne and 1,4-bis(biphenyl-4-yl)buta-1,3-diyne. Acta Crystallogr Sect C 62:o505–o509. doi:10.1107/S0108270106025157
Surette JKD, Macdonald MA, Zaworotko MJ, Singer RD (1994) X-ray crystal structure of 1,4-diphenylbutadiyne. J Chem Cryst 24(10):715–717. doi:10.1007/BF01668237
Mohr W, Stahl J, Hampel F, Gladysz JA (2003) Synthesis, structure, and reactivity of sp carbon chains with bis(phosphine) pentafluorophenylplatinum endgroups: butadiynediyl (C4) through hexadecaoctaynediyl (C16) bridges, and beyond. Chem Eur J 9(14):3324–3340. doi:10.1002/chem.200204741
Januszewski JA, Wendinger D, Methfessel CD, Hampel F, Tykwinski RR (2013) Synthesis and structure of tetraarylcumulenes: characterization of bond-length alternation versus molecule length. Angew Chem Int Ed 52(6):1817–1821. doi:10.1002/anie.201208058
Acknowledgments
Funding from the University of Erlangen-Nuremberg and the Deutsche Forschungsgemeinschaft (DFG SFB 953, Synthetic Carbon Allotropes) is gratefully acknowledged.
Author information
Authors and Affiliations
Corresponding author
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 2013 Springer-Verlag Berlin Heidelberg
About this chapter
Cite this chapter
Frankenberger, S., Januszewski, J.A., Tykwinski, R.R. (2013). Oligomers from sp-Hybridized Carbon: Cumulenes and Polyynes. In: Nierengarten, JF. (eds) Fullerenes and Other Carbon-Rich Nanostructures. Structure and Bonding, vol 159. Springer, Berlin, Heidelberg. https://doi.org/10.1007/430_2013_110
Download citation
DOI: https://doi.org/10.1007/430_2013_110
Published:
Publisher Name: Springer, Berlin, Heidelberg
Print ISBN: 978-3-642-54853-6
Online ISBN: 978-3-642-54854-3
eBook Packages: Chemistry and Materials ScienceChemistry and Material Science (R0)