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Sökning: onr:"swepub:oai:DiVA.org:uu-524634" > Syntheses and coord...

  • Huang, YanpingEast China Univ Sci & Technol, Key Lab Adv Mat, Shanghai 200237, Peoples R China.;East China Univ Sci & Technol, Sch Chem & Mol Engn, Shanghai Key Lab Funct Mat Chem, Inst Fine Chem,State Key Lab Bioreactor Engn,Sch P, Shanghai 200237, Peoples R China. (författare)

Syntheses and coordination of linear and macrocyclic pentapyrroles possessing a fused moiety : Confusion modulated structural diversity

  • Artikel/kapitelEngelska2024

Förlag, utgivningsår, omfång ...

  • Elsevier,2024
  • printrdacarrier

Nummerbeteckningar

  • LIBRIS-ID:oai:DiVA.org:uu-524634
  • https://urn.kb.se/resolve?urn=urn:nbn:se:uu:diva-524634URI
  • https://doi.org/10.1016/j.dyepig.2024.111948DOI
  • https://urn.kb.se/resolve?urn=urn:nbn:se:liu:diva-201451URI

Kompletterande språkuppgifter

  • Språk:engelska
  • Sammanfattning på:engelska

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Klassifikation

  • Ämneskategori:ref swepub-contenttype
  • Ämneskategori:art swepub-publicationtype

Anmärkningar

  • Funding Agencies|NSFC [22131005, 21971063, 22201074, 22075077]; Shanghai Rising -Star Program [23QA1402100]; Natural Science Foundation of Shanghai [23ZR1415600, 22ZR1416100]; Swedish Research Council [2018-05973, 2020-04600]
  • Porphyrinoids have attracted wide interest because of their vital roles in biological processes and fascinating structural and functional characters. In this work, a doubly N-confused pentapyrrane precursor N2C–P5 has been synthesized with terminal pyrrole ring A and middle pyrrole C incorporated in the N-confused mode. On this basis, pentapyrrin 1 and sapphyrin 2 have been synthesized by oxidizing N2C–P5 with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ). Both 1 and 2 possess a [5.5.5]-tricyclic fused ring involving pyrrole B and the neighboring confused pyrrole C. Meanwhile, the formation of 2 involves ring closure between the terminal rings A and E. Notably, 2 exists as a diradical showing a half-field signal in the electron paramagnetic resonance (EPR) spectrum and a singlet ground state with a negative singlet-triplet energy gap of −0.50 kcal/mol. Excellent thermal stability has been observed for 2, which may be related to its large π-conjugated framework involving the fused structure. On this basis, 1 and 2 were treated with Cu(acac)2 to afford Cu(II) complexes 3 and 4, respectively. As a result, an acetylacetonyl moiety is attached at the terminal pyrrole ring E to afford an NNNO coordination environment for complex 3, and the sapphyrin macrocycle of 2 has been cleaved between rings A and B to afford a fused pentapyrrin ligand, furnishing an NNNN coordination environment for complex 4, in which a pentafluorophenyl-ketal group generated during the ring cleavage reaction is attached to ring A, and it can be hydrolyzed to the corresponding pentafluorobenzoyl substituent to afford complex 5. Compared with free bases 1 and 2, complexes 3−5 show more intense low-energy near-infrared (NIR) absorption bands at ca. 791, 926 and 907 nm, respectively. This work provides an effective approach for the syntheses of linear and macrocyclic oligopyrroles with intriguing structures and properties by oxidizing oligopyrranes with precisely designed numbers and positions of N-confused pyrroles.

Ämnesord och genrebeteckningar

Biuppslag (personer, institutioner, konferenser, titlar ...)

  • Zhu, BinEast China Univ Sci & Technol, Key Lab Adv Mat, Shanghai 200237, Peoples R China.;East China Univ Sci & Technol, Sch Chem & Mol Engn, Shanghai Key Lab Funct Mat Chem, Inst Fine Chem,State Key Lab Bioreactor Engn,Sch P, Shanghai 200237, Peoples R China. (författare)
  • Li, QizhaoEast China Univ Sci & Technol, Key Lab Adv Mat, Shanghai 200237, Peoples R China.;East China Univ Sci & Technol, Sch Chem & Mol Engn, Shanghai Key Lab Funct Mat Chem, Inst Fine Chem,State Key Lab Bioreactor Engn,Sch P, Shanghai 200237, Peoples R China. (författare)
  • Baryshnikov, GlibLinköpings universitet,Laboratoriet för organisk elektronik,Tekniska fakulteten,Linköping Univ, Dept Sci & Technol, Lab Organ Elect, SE-60174 Norrköping, Sweden.(Swepub:liu)gliba58 (författare)
  • Li, ChengjieEast China Univ Sci & Technol, Key Lab Adv Mat, Shanghai 200237, Peoples R China.;East China Univ Sci & Technol, Sch Chem & Mol Engn, Shanghai Key Lab Funct Mat Chem, Inst Fine Chem,State Key Lab Bioreactor Engn,Sch P, Shanghai 200237, Peoples R China. (författare)
  • Sha, FengEast China Univ Sci & Technol, Key Lab Adv Mat, Shanghai 200237, Peoples R China.;East China Univ Sci & Technol, Sch Chem & Mol Engn, Shanghai Key Lab Funct Mat Chem, Inst Fine Chem,State Key Lab Bioreactor Engn,Sch P, Shanghai 200237, Peoples R China. (författare)
  • Wu, Xin-YanEast China Univ Sci & Technol, Key Lab Adv Mat, Shanghai 200237, Peoples R China.;East China Univ Sci & Technol, Sch Chem & Mol Engn, Shanghai Key Lab Funct Mat Chem, Inst Fine Chem,State Key Lab Bioreactor Engn,Sch P, Shanghai 200237, Peoples R China. (författare)
  • Ågren, HansUppsala universitet,Kemisk och biomolekylär fysik,Uppsala Univ, Sweden(Swepub:uu)hanag788 (författare)
  • Xie, YongshuEast China Univ Sci & Technol, Key Lab Adv Mat, Shanghai 200237, Peoples R China.;East China Univ Sci & Technol, Sch Chem & Mol Engn, Shanghai Key Lab Funct Mat Chem, Inst Fine Chem,State Key Lab Bioreactor Engn,Sch P, Shanghai 200237, Peoples R China. (författare)
  • East China Univ Sci & Technol, Key Lab Adv Mat, Shanghai 200237, Peoples R China.;East China Univ Sci & Technol, Sch Chem & Mol Engn, Shanghai Key Lab Funct Mat Chem, Inst Fine Chem,State Key Lab Bioreactor Engn,Sch P, Shanghai 200237, Peoples R China.Laboratoriet för organisk elektronik (creator_code:org_t)

Sammanhörande titlar

  • Ingår i:Dyes and pigments: Elsevier2230143-72081873-3743

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