Directed Metalation Cascade To Access Highly Functionalized Thieno[2,3-f]benzofuran and Exploration as Building Blocks for Organic Electronics

Abstract

A tandem directed metalation has been successfully applied to the preparation of thieno[2,3-f]benzofuran-4,8-dione, providing an efficient and facile approach to symmetrically and unsymmetrically functionalize the thieno[2,3-f]benzofuran core at the 2,6 positions as well as to introduce the electron-withdrawing or -donating groups (EWG or EDG) at its 4,8 positions. The presence of various functional groups makes late-stage derivatization attainable.

Constructive Quantum Interference in Single‐Molecule Benzodichalcogenophene Junctions

“…The target compounds I-III were prepared according to literature methods. [21] The single-molecule conductance measurementsw ere carriedo ut in aT HF/mesitylene solution (1:4, v/v) containing 0.1 mm target compound and tetrabutylammonium fluoride( TBAF,4equiv) using STM-BJ techniques, as sketched in Figure 1. [32] Our previous work [31] has demonstrated thatt he stable molecular junctions can be formedthrough the covalent bonds betweeng old electrodes and alkynylides generated by in situ desilylation in the presence of TBAF.…”

“…[17,20] Our aim is to investigate the effect of heteroatom substitution when the parent is an on-bipartite, aromatic molecule, stimulated in part by ad esire to understande lectron transport through benzodichalcogenophene (BDC) compounds, which possess ar igid and planar p-conjugated structurew ith strong electron-donating ability. [21,22] These properties have led to their use as organoelectronic compounds in dye-sensitized solar cells (DSSC), field effect transistors (OFET), organic lightemitting diodes (OLED)a nd in charge transports tudies of single molecules. [23][24][25][26][27][28][29] However the non-bipartite nature of the central core, the non-uniform bondinggeometry and structural rearrangement of typical anchoring groups in the junction, complicates the interpretationo fc harget ransport data.…”

Bis(Triphenylamine)Benzodifuran Chromophores: Synthesis, Electronic Properties and Application in Organic Light-Emitting Diodes

“…The symmetry and planarity as well as π-extended conjugation can enhance electron delocalization and intermolecular interactions and thus improve charge mobility. After recent explorations of facile and efficient synthetic methodologies, BDF derivatives, including small molecules and polymers, have been widely used for high performance organic electronics such as organic photovoltaics ( Li et al, 2010 ; Huo et al, 2012a ; Huo et al, 2012b ; Li et al, 2012 ; Aeschi et al, 2013 ; Li et al, 2013b ; Kularatne et al, 2013 ; Gao et al, 2020 ), organic field effect transistors (OFETs) ( Huang et al, 2014 ; Wang et al, 2016 ; Zhang et al, 2017 ; Wang et al, 2018 ), organic light-emitting diodes (OLEDs) ( Tsuji et al, 2007 ; Tsuji et al, 2009 ; Mitsui et al, 2012 ) and single-molecule devices ( Li et al, 2014 ; Huang et al, 2015 ; Xiang et al, 2015 ; Baghernejad et al, 2020 ). It has been demonstrated that extended π-conjugated BDF derivatives suitably functionalised with either pyridine ( Yi et al, 2010 ), or pyrene and anthracene ( Keller et al, 2011 ) or triphenyl amine (TPA) ( Faurie et al, 2018 ) termini show very strong fluorescence emission with luminescence quantum yields Φ F of up to 0.98.…”

Synthesis and photovoltaic properties of two new alkoxylphenyl substituted thieno[2,3-f]benzofuran based polymers

“…6,[20][21][22][23][24] Our group has also synthesized several 2D-conjugated BDT and BDF-based polymers and some of them have shown desirable performance. 28 Our group has recently reported a 2D-conjugated TBF-based polymer named PTBFTDTBT, which has reached an acceptable PCE of 6.4% without any device modifications or post-treatment. 28 Our group has recently reported a 2D-conjugated TBF-based polymer named PTBFTDTBT, which has reached an acceptable PCE of 6.4% without any device modifications or post-treatment.…”