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Chiral Teropyrenes: Synthesis, Structure, and Spectroscopic Studies.
Bam, Radha; Yang, Wenlong; Longhi, Giovanna; Abbate, Sergio; Lucotti, Andrea; Tommasini, Matteo; Franzini, Roberta; Villani, Claudio; Catalano, Vincent J; Olmstead, Marilyn M; Chalifoux, Wesley A.
Afiliación
  • Bam R; Department of Chemistry, University of Nevada, Reno, 1664 N. Virginia St., Reno, Nevada, 89557, USA.
  • Yang W; Department of Chemistry, University of Nevada, Reno, 1664 N. Virginia St., Reno, Nevada, 89557, USA.
  • Longhi G; Dipartimento di Medicina Molecolare e Traslazionale, Università degli Studi di Brescia, Viale Europa 11, 25123, Brescia, Italy.
  • Abbate S; Dipartimento di Medicina Molecolare e Traslazionale, Università degli Studi di Brescia, Viale Europa 11, 25123, Brescia, Italy.
  • Lucotti A; Dipartimento di Chimica, Materiali e Ingegneria Chimica "G. Natta,", Politecnico di Milano, Piazza Leonardo da Vinci 32, 20133, Milano, Italy.
  • Tommasini M; Dipartimento di Chimica, Materiali e Ingegneria Chimica "G. Natta,", Politecnico di Milano, Piazza Leonardo da Vinci 32, 20133, Milano, Italy.
  • Franzini R; Dipartimento di Chimica e Tecnologie del Farmaco, Università di Roma "La Sapienza", 00185, Roma, Italy.
  • Villani C; Dipartimento di Chimica e Tecnologie del Farmaco, Università di Roma "La Sapienza", 00185, Roma, Italy.
  • Catalano VJ; Department of Chemistry, University of Nevada, Reno, 1664 N. Virginia St., Reno, Nevada, 89557, USA.
  • Olmstead MM; Department of Chemistry, University of California, Davis, One Shields Avenue, Davis, California, 95616, USA.
  • Chalifoux WA; Department of Chemistry, University of Nevada, Reno, 1664 N. Virginia St., Reno, Nevada, 89557, USA.
Angew Chem Int Ed Engl ; 63(33): e202404849, 2024 Aug 12.
Article en En | MEDLINE | ID: mdl-38818567
ABSTRACT
We present the inaugural synthesis of a chiral teropyrene achieved through a four-fold alkyne benzannulation catalyzed by InCl3, resulting in good yields. The product underwent thorough characterization using FT-Raman and FT-IR spectroscopies, demonstrating a close agreement with calculated spectra. X-ray crystallographic analysis unveiled a notable twist in the molecule's backbone, with an end-to-end twist angle of 51°, consistent with computational predictions. Experimentally determined enantiomeric inversion barriers revealed a significant energy barrier of 23 kcal/mol, facilitating the isolation of enantiomers for analysis by circular dichroism (CD) and circularly polarized luminescence (CPL) spectroscopies. These findings mark significant strides in the synthesis and characterization of chiral teropyrenes, offering insights into their structural and spectroscopic properties.
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Idioma: En Revista: Angew Chem Int Ed Engl Año: 2024 Tipo del documento: Article País de afiliación: Estados Unidos Pais de publicación: Alemania
Texto completo
Añadir a Mi BVS
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XML
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Idioma: En Revista: Angew Chem Int Ed Engl Año: 2024 Tipo del documento: Article País de afiliación: Estados Unidos Pais de publicación: Alemania