메뉴 건너뛰기




Volumn 7, Issue 19, 2009, Pages 3958-3968

Microwave-assisted synthesis of a new series of resorcin[4]arene Cavitand-capped porphyrin capsules

Author keywords

[No Author keywords available]

Indexed keywords

CAVITANDS; ENZYMATIC PROCESS; HEMICARCERAND; HOST GUEST INTERACTIONS; HOST MOLECULES; IN-SITU; MICROWAVE ASSISTED SYNTHESIS; MOLECULAR CAPSULE; MOLECULAR RECEPTORS; NEW SERIES; REFLUXING; SYNTHETIC RECEPTORS;

EID: 70349286093     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/b907547j     Document Type: Article
Times cited : (8)

References (62)
  • 20
    • 33748716824 scopus 로고    scopus 로고
    • J. L. Atwood, J. E. D. Davies, D. D. Macnicol, F. Vogtle, D. N. Reinhoudt and J.-M. Lehn, Pergamon, Elmsford, pp. 267-360
    • M. C. Feiters, in Comprehensive Supramolecular Chemistry, eds., J. L. Atwood, J. E. D. Davies, D. D. Macnicol, F. Vogtle, D. N. Reinhoudt, and, J.-M. Lehn, Pergamon, Elmsford, 1996, vol. 10, pp. 267-360
    • (1996) Comprehensive Supramolecular Chemistry, Eds.
    • Feiters In, M.C.1
  • 33
    • 33748716824 scopus 로고    scopus 로고
    • J. L. Atwood, J. E. D. Davies, D. D. Macnicol, F. Vogtle, D.N. Reinhoudt and J.-M. Lehn, Pergamon, Elmsford, pp. 367-418
    • E. F. Maverick and D. J. Cram, in Comprehensive Supramolecular Chemistry, eds., J. L. Atwood, J. E. D. Davies, D. D. Macnicol, F. Vogtle, D.N. Reinhoudt, and, J.-M. Lehn, Pergamon, Elmsford, 1996, vol. 2, pp. 367-418
    • (1996) Comprehensive Supramolecular Chemistry, Eds.
    • Maverick, E.F.1    Cram In, D.J.2
  • 41
    • 70349295924 scopus 로고    scopus 로고
    • The TPP derivative used consists as a mixture of four isomers, varying only in the orientation of the o-hydroxy groups. Isomerisation occurs at room temperature, and reflux of the reaction solution, as observed by Naruta and co-workers. This results in the correct orientation (over a period of days) of all the hydroxy groups to afford coupling of the porphyrin with the resorcin[4]arene. Altering reflux temperatures and lengths were among the changes made to protocol
    • The TPP derivative used consists as a mixture of four isomers, varying only in the orientation of the o-hydroxy groups. Isomerisation occurs at room temperature, and reflux of the reaction solution, as observed by Naruta and co-workers. This results in the correct orientation (over a period of days) of all the hydroxy groups to afford coupling of the porphyrin with the resorcin[4]arene. Altering reflux temperatures and lengths were among the changes made to protocol
  • 42
    • 70349282190 scopus 로고    scopus 로고
    • Preparation of supramolecularly capped porphyrins from aldehyde precursors such as 3 and 4 has been shown to proceed via two synthetic pathways. The most common of these two methods makes use of the Adler conditions; the addition of pyrrole to the aldehyde followed by condensation in an acidic medium (propionic acid) at reflux temperatures (140 °C) under aerobic conditions. In contrast, the gentler Lindsey conditions make use of a Lewis acid catalyst and dry, inert reaction conditions. This latter protocol has found only limited application. However, observations by Reinhoudt et al. indicated that porphyrin formation using this cyclisation technique was significantly dependant on the synthetic conditions employed. Ligands bearing shorter bridges formed exclusively on application of the Adler conditions, whilst ligands bearing longer bridges exclusively on application of the Lindsey conditions
    • Preparation of supramolecularly capped porphyrins from aldehyde precursors such as 3 and 4 has been shown to proceed via two synthetic pathways. The most common of these two methods makes use of the Adler conditions; the addition of pyrrole to the aldehyde followed by condensation in an acidic medium (propionic acid) at reflux temperatures (140 °C) under aerobic conditions. In contrast, the gentler Lindsey conditions make use of a Lewis acid catalyst and dry, inert reaction conditions. This latter protocol has found only limited application. However, observations by Reinhoudt et al. indicated that porphyrin formation using this cyclisation technique was significantly dependant on the synthetic conditions employed. Ligands bearing shorter bridges formed exclusively on application of the Adler conditions, whilst ligands bearing longer bridges exclusively on application of the Lindsey conditions
  • 59
    • 70349274386 scopus 로고    scopus 로고
    • The microwave synthesis unit used did not allow for variable power output. Additionally, the borosilicate reaction vessels used were of a fixed volume, which limited studies of the effect of varied reagent concentration on yield
    • The microwave synthesis unit used did not allow for variable power output. Additionally, the borosilicate reaction vessels used were of a fixed volume, which limited studies of the effect of varied reagent concentration on yield
  • 60
    • 70349277489 scopus 로고    scopus 로고
    • Optimum yields were obtained for a reagent concentration of 0.01 M (with respect to aldehyde precursor). Increasing concentrations to 0.02 M (at every temperature) had no observable effect on yield
    • Optimum yields were obtained for a reagent concentration of 0.01 M (with respect to aldehyde precursor). Increasing concentrations to 0.02 M (at every temperature) had no observable effect on yield


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.