TY - JOUR
T1 - A non-tetradecarboxylative synthesis of 2,7,12,17-tetraphenylporphycene
AU - Gavalda, Ana
AU - Borrell, JosÉ I.
AU - Teixido, Jordi
AU - Nonell, Santiago
AU - Arad, Ofir
AU - Grau, Roser
AU - CaÑete, Magdalena
AU - Juarranz, Angeles
AU - Villanueva, Angeles
AU - Stockert, Juan C.
PY - 2001/12
Y1 - 2001/12
N2 - A new synthetic method for 2,7,12,17-tetraphenylporphycene (2e, TPPo) which avoids tetradecarboxylation by sublimation of the intermediate tetracarboxylic acid 8 is reported. Thus, the use of a pyrrol 13a bearing two orthogonal ester groups allows the synthesis of bipyrrol 12a, from which the benzyl ester groups are selectively removed to afford diester 11. The latter is transformed to dialdehyde 10 by using the McFayden-Stevens reaction, thus avoiding the unstable bipyrrol 9 formed during the tetradecarboxylation of 8.
AB - A new synthetic method for 2,7,12,17-tetraphenylporphycene (2e, TPPo) which avoids tetradecarboxylation by sublimation of the intermediate tetracarboxylic acid 8 is reported. Thus, the use of a pyrrol 13a bearing two orthogonal ester groups allows the synthesis of bipyrrol 12a, from which the benzyl ester groups are selectively removed to afford diester 11. The latter is transformed to dialdehyde 10 by using the McFayden-Stevens reaction, thus avoiding the unstable bipyrrol 9 formed during the tetradecarboxylation of 8.
KW - Orthogonal protecting groups
KW - Photodynamic therapy, (PDT)
KW - Porphycene
KW - Sensitizer
KW - Tetraphenylporphycene
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UR - https://www.webofscience.com/api/gateway?GWVersion=2&SrcApp=pure_univeritat_ramon_llull&SrcAuth=WosAPI&KeyUT=WOS:000173573800006&DestLinkType=FullRecord&DestApp=WOS_CPL
U2 - 10.1002/jpp.552
DO - 10.1002/jpp.552
M3 - Article
AN - SCOPUS:0035699426
SN - 1088-4246
VL - 5
SP - 846
EP - 852
JO - Journal of Porphyrins and Phthalocyanines
JF - Journal of Porphyrins and Phthalocyanines
IS - 12
ER -