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Volumn 50, Issue 10, 2011, Pages 2280-2283

Metal-mediated synthesis of antiaromatic porphyrinoids from a BODIPY precursor

Author keywords

Annulenes; Aromaticity; Cross coupling; Dyes pigments; Porphyrinoids

Indexed keywords

ANNULENES; AROMATICITY; CROSS-COUPLINGS; DYES/PIGMENTS; PORPHYRINOIDS;

EID: 79952061519     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201006314     Document Type: Article
Times cited : (68)

References (41)
  • 1
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    • (Eds.: K. M. Kadish, K. M. Smith, K. R. Guilard), Academic Press, San Diego
    • The Porphyrin Handbook, Vol. 1 (Eds.: K. M. Kadish, K. M. Smith, K. R. Guilard), Academic Press, San Diego, 2000.
    • (2000) The Porphyrin Handbook , vol.1
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    • (Eds.: K. M. Kadish, K. M. Smith, K. R. Guilard), World Scientific, New Jersey
    • c) A. Loudet, K. Burgess in Handbook of Porphyrin Science, Vol. 8 (Eds.: K. M. Kadish, K. M. Smith, K. R. Guilard), World Scientific, New Jersey, 2010, p. 1.
    • (2010) Handbook of Porphyrin Science , vol.8 , pp. 1
    • Loudet, A.1    Burgess, K.2
  • 10
    • 42949084702 scopus 로고    scopus 로고
    • For boron complexes of porphyrinoids, see
    • For boron complexes of porphyrinoids, see: P. J. Brothers, Chem. Commun. 2008, 2090.
    • (2008) Chem. Commun. , pp. 2090
    • Brothers, P.J.1
  • 15
    • 75149198661 scopus 로고    scopus 로고
    • We also attempted Sonogashira coupling for the synthesis of 2, but Stille coupling gave a better result
    • c) M. R. Rao, S. M. Mobin, M. Ravikanth, Tetrahedron 2010, 66, 1728. We also attempted Sonogashira coupling for the synthesis of 2, but Stille coupling gave a better result.
    • (2010) Tetrahedron , vol.66 , pp. 1728
    • Rao, M.R.1    Mobin, S.M.2    Ravikanth, M.3
  • 30
    • 79952057988 scopus 로고    scopus 로고
    • w = 0.3499 (all data), GOF = 0.957 (I > 2.0σ(I))
    • w = 0.2251 (all data), GOF=1.032 (I > 2.0σ(I)). CCDC-795975 (2′), 795976 (3), 795977 (4′), and 795978 (5) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data- request/cif.
  • 31
    • 27744530363 scopus 로고    scopus 로고
    • The NICS value has been successfully used as a measure of aromaticity, see: a
    • The NICS value has been successfully used as a measure of aromaticity, see: a) Z. Chen, C. S. Wannere, C. Corminboeuf, R. Puchta, P. von R. Schleyer, Chem. Rev. 2005, 105, 3842;
    • (2005) Chem. Rev. , vol.105 , pp. 3842
    • Chen, Z.1    Wannere, C.S.2    Corminboeuf, C.3    Puchta, R.4    Von Schleyer, P.R.5
  • 33
    • 79952065253 scopus 로고    scopus 로고
    • note
    • The optimized structure of 4 takes a completely flat conformation with an NICS value of +8.1 ppm. These results imply a somewhat more flexible nature of 4 in comparison to the rigid dimer 3.
  • 34
    • 79952044889 scopus 로고    scopus 로고
    • note
    • -1.
  • 35
    • 79952052912 scopus 로고    scopus 로고
    • note
    • No emission peak was detected in the range 1000-1500 nm.
  • 39
    • 79952052552 scopus 로고    scopus 로고
    • note
    • -1.
  • 41
    • 79952051066 scopus 로고    scopus 로고
    • note
    • DFT calculations for 5 at the B3LYP/6-31G(d) level suggested the involvement of through-bond interactions between molecular orbitals of two BODIPY units (Figure S33).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.