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Volumn 128, Issue 51, 2006, Pages 16740-16747

Giant macrocycles composed of thiophene, acetylene, and ethylene building blocks

Author keywords

[No Author keywords available]

Indexed keywords

ACETYLENE; CYCLIC VOLTAMMETRY; DERIVATIVES; ETHYLENE; SUBSTITUTION REACTIONS; SULFUR COMPOUNDS; SYNTHESIS (CHEMICAL);

EID: 33845948753     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja067077t     Document Type: Article
Times cited : (167)

References (135)
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    • (1992) Chem. Rew , vol.92 , pp. 711-738
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    • Diederich, F, Stang, P. J, Tykwinski, R. R, Eds, Wiley-VCH Weinheim
    • (g) Acetylene Chemistry; Diederich, F.; Stang, P. J.; Tykwinski, R. R., Eds.; Wiley-VCH Weinheim, 2005.
    • (2005) Acetylene Chemistry
  • 53
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    • Hori, T.; Aratani, N.; Takagi, A.; Matsumoto, T.; Kawai, T.; Yoon, M.-C.; Yoon, Z. S.; Cho, S.; Kim, D.; Osuka, A. Chem.-Eur. J. 2006, 112, 1319-1327.
    • (f) Hori, T.; Aratani, N.; Takagi, A.; Matsumoto, T.; Kawai, T.; Yoon, M.-C.; Yoon, Z. S.; Cho, S.; Kim, D.; Osuka, A. Chem.-Eur. J. 2006, 112, 1319-1327.
  • 104
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    • The inner diameters of 1-6 were estimated based on PM3 calculations of unsubstituted cyclic compounds 1b-6b. AM1 calculations led to similar results.
    • The inner diameters of 1-6 were estimated based on PM3 calculations of unsubstituted cyclic compounds 1b-6b. AM1 calculations led to similar results.
  • 108
  • 113
    • 33845921136 scopus 로고    scopus 로고
    • 3 as eluent]. Because 1a easily crystallizes from hexane and chloroform, the separation of 1a from its E,Z and Z,Z isomers and 2a-5a is also easy to do. In concern for E,Z and Z,Z isomers of 2a-5a, their formation was not observed, and only pure E,E-isomers of 2a-5a were isolated and characterized.
    • 3 as eluent]. Because 1a easily crystallizes from hexane and chloroform, the separation of 1a from its E,Z and Z,Z isomers and 2a-5a is also easy to do. In concern for E,Z and Z,Z isomers of 2a-5a, their formation was not observed, and only pure E,E-isomers of 2a-5a were isolated and characterized.
  • 122
    • 0029378646 scopus 로고    scopus 로고
    • 6+: Tol, A. W. J. Synth. Met. 1995, 74, 95-98.
    • 6+: Tol, A. W. J. Synth. Met. 1995, 74, 95-98.
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    • 33845944359 scopus 로고    scopus 로고
    • +) of 15 are much higher than 1a-6a. HOMO level of 15 is also lower than those of 1a-6a based on PM3 calculations.
    • +) of 15 are much higher than 1a-6a. HOMO level of 15 is also lower than those of 1a-6a based on PM3 calculations.
  • 131
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    • Doping of iodine vapor was carried out using a compressed pellet of ca. 1 × 0.5 × 0.01 mm3 size, to which two gold wires were attached apart through ca. 0.5 mm distance. Before doping, each sample prepared from 1a-3a was an insulator. After doping of iodine vapor for 5-70. min, all samples showed electric conductivities.
    • Doping of iodine vapor was carried out using a compressed pellet of ca. 1 × 0.5 × 0.01 mm3 size, to which two gold wires were attached apart through ca. 0.5 mm distance. Before doping, each sample prepared from 1a-3a was an insulator. After doping of iodine vapor for 5-70. min, all samples showed electric conductivities.
  • 134
    • 33645753534 scopus 로고    scopus 로고
    • Macrocyclic cyclo[n]thiophenes less than n = 14 are calculated to possess s-cisoid conformation with a planar structure, but larger cyclic oligothiophenes adopt a more energetically favorable s-transoid conformation: Zade, S. S.; Bendikov, M. J. Org. Chem. 2006, 71, 2972-2981.
    • Macrocyclic cyclo[n]thiophenes less than n = 14 are calculated to possess s-cisoid conformation with a planar structure, but larger cyclic oligothiophenes adopt a more energetically favorable s-transoid conformation: Zade, S. S.; Bendikov, M. J. Org. Chem. 2006, 71, 2972-2981.
  • 135
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    • The energy differences between planar and nonplanar conformations of 3b-5b are less than 1 kcal/mol based on PM3 calculations.
    • The energy differences between planar and nonplanar conformations of 3b-5b are less than 1 kcal/mol based on PM3 calculations.


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