Synthesis, Optical, and Redox Properties of Regioisomeric Benzoheterocycles-Fused Pyrene.

A new synthetic route toward the synthesis of benzo[b]phospholes- and benzo[b]siloles-fused pyrenes using a transition metal-catalyzed C-H bond activation is described. The compounds were fully characterized including X-ray diffraction. A combined experimental and theoretical study shows that both the heteroatom and the substitution pattern impact the optical and redox properties.

[1]  Z. Ding,et al.  Synthesis, structures and photophysical properties of two regioisomeric phenalenocarbazoles. , 2018, Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy.

[2]  A. Mateo‐Alonso.  Synthetic Approaches to Pyrene‐Fused Twistacenes , 2017 .

[3]  A. Dreuw,et al.  K-Region-Extended [c]-Heteroannulated Pyrenes. , 2017, Chemistry.

[4]  M. Hissler,et al.  Phosphorus-Containing Polycyclic Aromatic Hydrocarbons. , 2017, Chemphyschem : a European journal of chemical physics and physical chemistry.

[5]  M. Stępień,et al.  Heterocyclic Nanographenes and Other Polycyclic Heteroaromatic Compounds: Synthetic Routes, Properties, and Applications. , 2017, Chemical reviews.

[6]  M. Hissler,et al.  π -Conjugated Phospholes and their Incorporation into Devices; A Component with a Great Deal of Potential , 2016 .

[7]  C. Redshaw,et al.  Functionalization of Pyrene To Prepare Luminescent Materials-Typical Examples of Synthetic Methodology. , 2016, Chemistry.

[8]  M. Hissler,et al.  Organophosphorus derivatives for electronic devices , 2016 .

[9]  Zhi-qiang Liu,et al.  Synthesis, structure and photophysical properties of regioisomeric sulfone-bridged pyrene–thienoacenes , 2015 .

[10]  M. Hissler,et al.  Edge modification of PAHs: the effect of embedded heterocycles on the aromaticity pattern , 2015, Structural Chemistry.

[11]  K. Müllen,et al.  New advances in nanographene chemistry. , 2015, Chemical Society reviews.

[12]  Jongwook Park,et al.  Synthesis and Electroluminescence of Novel Pyrene-Fused Chromophores. , 2015, Organic letters.

[13]  Robert M. Edkins,et al.  Electron Delocalization in Reduced Forms of 2-(BMes2)pyrene and 2,7-Bis(BMes2)pyrene. , 2015, Journal of the American Chemical Society.

[14]  Robert M. Edkins,et al.  Synthesis and photophysics of a 2,7-disubstituted donor-acceptor pyrene derivative: an example of the application of sequential Ir-catalyzed C-H borylation and substitution chemistry. , 2015, The Journal of organic chemistry.

[15]  Arunandan Kumar,et al.  Phosphine oxide functionalized pyrenes as efficient blue light emitting multifunctional materials for organic light emitting diodes , 2015 .

[16]  N. Chatani,et al.  Palladium‐Catalyzed Direct Synthesis of Phosphole Derivatives from Triarylphosphines Through Cleavage of Carbon—Hydrogen and Carbon—Phosphorus Bonds. , 2014 .

[17]  A. P. Davis,et al.  Synthesis of substituted pyrenes by indirect methods. , 2014, Organic & biomolecular chemistry.

[18]  Robert M. Edkins,et al.  Synthesis, structure, and opto-electronic properties of regioisomeric pyrene-thienoacenes. , 2014, Organic letters.

[19]  N. Chatani,et al.  Palladium-catalyzed direct synthesis of phosphole derivatives from triarylphosphines through cleavage of carbon-hydrogen and carbon-phosphorus bonds. , 2013, Angewandte Chemie.

[20]  T. Baumgartner,et al.  Combining form with function--the dawn of phosphole-based functional materials. , 2012, Dalton transactions.

[21]  J. Howard,et al.  Synthesis of 2- and 2,7-functionalized pyrene derivatives: an application of selective C-H borylation. , 2012, Chemistry.

[22]  T. Baumgartner,et al.  Structure–Property Studies of Bichromophoric, PAH-Functionalized Dithieno[3,2-b:2′,3′-d]phospholes , 2012 .

[23]  K. Takai,et al.  Palladium-catalyzed synthesis of dibenzophosphole oxides via intramolecular dehydrogenative cyclization. , 2011, The Journal of organic chemistry.

[24]  Andreas Steffen,et al.  Experimental and theoretical studies of the photophysical properties of 2- and 2,7-functionalized pyrene derivatives. , 2011, Journal of the American Chemical Society.

[25]  Klaus Müllen,et al.  Pyrene-based materials for organic electronics. , 2011, Chemical reviews.

[26]  Kazuhiko Takai,et al.  Rhodium-catalyzed synthesis of silafluorene derivatives via cleavage of silicon-hydrogen and carbon-hydrogen bonds. , 2010, Journal of the American Chemical Society.

[27]  S. Barlow,et al.  Substituent effects on the electronic structure of siloles. , 2009, Chemical communications.

[28]  Y. Matano,et al.  Design and synthesis of phosphole-based pi systems for novel organic materials. , 2009, Organic & biomolecular chemistry.

[29]  L. Daniels,et al.  Synthesis and crystal structures of fluorescent receptors for 9-butyladenine , 2009 .

[30]  N. Turro,et al.  Principles of Molecular Photochemistry: An Introduction , 2008 .

[31]  Wojciech Pisula,et al.  Graphenes as potential material for electronics. , 2007, Chemical reviews.

[32]  Jianliang Xiao,et al.  Palladium-catalysed synthesis of biaryl phosphines , 2004 .

[33]  K. Tamao,et al.  Bis-silicon-bridged stilbene homologues synthesized by new intramolecular reductive double cyclization. , 2003, Journal of the American Chemical Society.

[34]  M. Hissler,et al.  Linear organic π-conjugated systems featuring the heavy Group 14 and 15 elements , 2003 .

[35]  T. Roisnel,et al.  A Dihydrodinaphthoheptacene. , 2018, The Journal of organic chemistry.

[36]  L. Nyulászi,et al.  Aromatic Phosphorus Heterocycles , 2008 .