Benzofuran-/Benzothiophene-Incorporated NIR-Absorbing Triphyrins(2.1.1).

Novel benzofuran-/benzothiophene-incorporated triphyrins(2.1.1) were synthesized using readily available precursors under mild reaction conditions. The X-ray structure revealed that the benzofuran-incorporated triphyrin(2.1.1) macrocycle was slightly ruffled. The triphyrins(2.1.1) exhibit more absorption in the NIR region compared to previously reported dibenzofuran-/dibenzothiophene-incorporated hybrid macrocycles. The benzofuran-incorporated triphyrin shows significant red shift in absorption bands compared to that of benzothiophene-based triphyrin due to its more coplanar arrangement as supported by X-ray and DFT studies.

[1]  Ankita Kumar,et al.  Hybrid Macrocycles of Subporphyrins and Triphyrins. , 2017, Organic Letters.

[2]  Soji Shimizu Recent Advances in Subporphyrins and Triphyrin Analogues: Contracted Porphyrins Comprising Three Pyrrole Rings. , 2017, Chemical reviews.

[3]  T. Sarma,et al.  Annulated Isomeric, Expanded, and Contracted Porphyrins. , 2017, Chemical reviews.

[4]  N. Aratani,et al.  Synthesis and Characterization of an Iridium Triphyrin Complex. , 2016, Inorganic chemistry.

[5]  Arun Kumar,et al.  Bipyricorrole: A Corrole Homologue with a Monoanionic Core as a Fluorescence Zn(II) Sensor. , 2016, Angewandte Chemie.

[6]  C. Suresh,et al.  A 6,11,16-Triarylbiphenylcorrole with an adj-CCNN Core: Stabilization of an Organocopper(III) Complex. , 2015, Angewandte Chemie.

[7]  A. Białońska,et al.  Phenanthriporphyrin: an antiaromatic aceneporphyrinoid as a ligand for a hypervalent organophosphorus(V) moiety. , 2015, Angewandte Chemie.

[8]  Dongho Kim,et al.  Subporphyrinato boron(III) hydrides. , 2015, Journal of the American Chemical Society.

[9]  K. Ohkubo,et al.  η5-Cyclopentadienyliron(II)-[14]triphyrin(2.1.1) sandwich compounds: synthesis, characterization, and stable redox interconversion. , 2013, Angewandte Chemie.

[10]  H. Yamada,et al.  Synthesis and characterization of new platinum(II) and platinum(IV) triphyrin complexes. , 2013, Inorganic chemistry.

[11]  Byung Sun Lee,et al.  Photophysical analysis of 1,10-phenanthroline-embedded porphyrin analogues and their magnesium(II) complexes. , 2012, Chemistry.

[12]  N. Aratani,et al.  Effective meso fabrications of subporphyrins. , 2012, Angewandte Chemie.

[13]  H. Yamada,et al.  New synthesis of meso-free-[14]triphyrin(2.1.1) by McMurry coupling and its derivatization to Mn(I) and Re(I) complexes. , 2011, Chemical communications.

[14]  F. Tani,et al.  A porphyrin-related macrocycle with an embedded 1,10-phenanthroline moiety: fluorescent magnesium(II) ion sensor. , 2010, Angewandte Chemie.

[15]  X. You,et al.  A facile one-pot synthesis of meso-aryl-substituted [14]triphyrin(2.1.1). , 2008, Journal of the American Chemical Society.

[16]  A. Osuka,et al.  Subporphyrins: emerging contracted porphyrins with aromatic 14pi-electronic systems and bowl-shaped structures: rational and unexpected synthetic routes. , 2008, Dalton transactions.

[17]  A. Matsuda,et al.  Synthesis and characterization of meso-triarylsubporphyrins. , 2007, Journal of the American Chemical Society.

[18]  Dongho Kim,et al.  meso-Aryl-substituted subporphyrins: synthesis, structures, and large substituent effects on their electronic properties. , 2007, Journal of the American Chemical Society.

[19]  T. Lis,et al.  Dithiaethyneporphyrin: an atypical [18]triphyrin(4.1.1) frame for contracted porphyrins. , 2005, Angewandte Chemie.

[20]  E. Vogel Porphyrinoid macrocycles: A cornucopia of novel chromophores , 1996 .