The development of conjugated organic materials has become a rapidly evolving field research, particularly with view toward practical applications in so-called electronics that encompass variety device types, such as OLEDs, OPVs, and OFETs. Almost all these devices minimally require the presence electron-donor -acceptor components act p- n-type semiconductors, respectively. Research over past two decades shown while there is an abundant resource p-type materials, suitable species are few far...

Phosphole-based π-conjugated compounds have recently attracted significant attention due their unique electronic properties. It is now well established that the versatile phosphorus chemistry offers great opportunities for efficient fine-tuning of properties systems from a fundamental point view; feature pure carbon-based materials cannot provide. This perspective highlights recent progress using phosphole-based building blocks towards applied with multiple and diverse functionalities.

The systematic extension of the pi-conjugated system strongly blue-luminescent dithieno[3,2-b:2',3'-d]phospholes has been investigated with goal obtaining different emission colors. Functionalization 2- and 6-position dithienophosphole scaffold halogen substituents provided functional building blocks for subsequent cross-coupling experiments various homo- heteroaryls to selectively decrease band gap materials. By this strategy materials colors ranging from green via yellow orange could be...

The syntheses and the electrochemical spectroscopic properties of a suite asymmetrical bistridentate cyclometalated Ru(II) complexes bearing terminal triphenylamine (TPA) substituents are reported. These complexes, which contain structural design elements common to both inorganic organic dyes that exhibit superior power conversion efficiencies in dye-sensitized solar cell (DSSC), broadly formulated as [RuII(L-2,5′-thiophene-TPA-R1)(L-R2)]+ [L = tridentate chelating ligand (e.g.,...

The last decade has witnessed great progress in conjugated polymers for application optoelectronics. biggest driving force the field is to develop with suitable HOMO and LUMO orbital energies, as well high charge carrier mobility improved performance practical devices. Apart from conventional donor–acceptor (D–A) strategy tune optoelectronic properties, incorporation of main-group elements represents a promising new way achieve similar function, however, more efficiently, due intrinsic...

Phosphorus-based materials have received widespread attention in recent years, particular as possible candidates for practical application organic electronics. The geometry and electronic nature of phosphorus make it a favorable heteroatom property tuning order to obtain better performing This Focus Review discusses structural modifications syntheses phosphorus-based materials, illustrates at the same time, highlights specific examples device applications.

A series of new amphiphilic phosphonium materials that combine the electronic features phospholes with self-assembly lipids were synthesized. Variable concentration/temperature and 2D NMR studies suggested systems undergo intramolecular conformation changes between a "closed" "open" form are triggered by intermolecular interactions. The phospholium species also induce liquid crystalline soft crystal phase behavior in solid state, which was studied differential scanning calorimetry (DSC),...

Benzo-condensed dithieno[3,2-b:2',3'-d]phospholes have been synthesized that allow convenient tuning of properties are essential for application as semiconductor materials in organic field-effect transistor (OFET) devices. The versatile reactivity the trivalent phosphorus atom these heteropentacenes provides access to a series show different photophysical properties, significantly organization solid state, and distinctly electrochemical can be achieved by simple chemical modifications....

A simple and representative procedure for the synthesis of N,N'-diarylated phosphaviologens directly from both electron-rich electron-poor diaryliodonium salts 2,7-diazadibenzophosphole oxide is reported. The latter are electron-deficient congeners widely utilized N,N'-disubstituted 4,4'-bipyridinium cations, also known as viologens, that proved to be inaccessible by classical two-step route. single-step preparation method described herein could extended genuine viologens but reached its...

We report a structure-property study on phosphoryl-bridged viologen analogues with remarkably low reduction threshold. Utilizing different benzyl groups for N-quaternization, we were able to confirm the p-benzyl substituent effect electronic tunability of system while maintaining characteristic chromic response viologens two fully reversible one-electron reductions. Due considerably increased electron-acceptor properties bipyridine precursor, N-benzylation was found be very challenging and...

New ladder-type, phosphorus- and sulfur-based heterotetracenes were synthesized, which allowed the engineering of materials' properties by exploitation different reactivities between sulfur phosphorus. (31)P NMR spectroscopy X-ray crystallographic studies revealed that electronic effects secondary heteroatom, sulfur, influence not only conjugation in heterotetracene core but also behavior phosphorus center. UV-vis fluorescence showed scaffold's band gap is mainly controlled nature while...

ConspectusRecent ground-breaking advances in synthetic chemistry have transformed main-group molecules from simple laboratory curiosities into powerful materials for a range of applications all realms life. Electron-accepting or -deficient materials, particular, been the focus development since their generally limited availability and stability major hurdles establishing new practical applications. In addition to general requirements design these deeper understanding inherent electronics...

To explore their suitability for applications in molecular optoelectronics and as sensory materials, novel dithieno[3,2-b:2',3'-d]phospholes have been synthesized reactivity properties investigated. An efficient two-step synthesis allowed a modular assembly of differently functionalized compounds. The dithieno[3,2-b:2',3'-d]phosphole system exhibits extraordinary optoelectronic with respect to wavelength, intensity, tunability. Owing the nucleophilic nature central phosphorus atom, its...

Abstract The introduction of phosphorus‐containing moieties into π‐conjugated thiophene materials has been found to provide with strongly optimized and highly tunable optoelectronic features compared their native counterparts. 2,5‐Diaryl‐ 2,5‐bis(heteroaryl)phospholes as well fused tricyclic dithieno[3,2‐ b :2′,3′‐ d ]phospholes represent two very valuable building blocks for organic electronics intriguing can be altered systematically by several, in part unique, methodologies. potential...

Sensitive gels: The amphiphilic features of phosphole-lipids lead to intriguing self-assembly properties and the formation highly fluorescent organogels. Moreover, dynamic structural system make it possible amplify mechanochromic emission shifts (100 nm) in a donor–acceptor through thermally mechanically responsive fluorescence resonance energy transfer (FRET).

Phosphorus pulls its weight: Installation of a phosphoryl group as central bridge in the 4,4′-bipyridine scaffold introduces improved reduction responses that become even more pronounced corresponding phosphoryl-bridged methylviologen (see picture). Importantly, maintains typical viologen optical response upon reversible reduction, however, at much lower potentials. Detailed facts importance to specialist readers are published "Supporting Information". Such documents peer-reviewed, but not...

Abstract This paper describes a structure–property study using two dithieno[3,2‐ b ;2′,3′‐ d ]phosphole building blocks for the generation of white light emission and incorporation these units in single polystyrene material. The one light‐emitting organophosphorus can efficiently be switched from orange to green by simple protonation amino functional groups that are part π ‐conjugated scaffold. resulting three components (blue, green, orange) exhibit photophysical properties allow an...

A series of conjugated materials based on the new dithieno[3,2-c:2',3'-e]-2,7-diketophosphepin (DTDKP) building block have been studied for first time. Theoretical calculations predict DTDKP to be a better electron acceptor than well-known dithienophosphole and nitrogen analogue, bithiopheneimide. Cyclic voltammetry studies revealed two reduction processes that support their promising electron-acceptor properties, modification P center with O or gold(I) further reduced LUMO energy ca. -3.6...

Conjugated materials have attracted much attention toward applications in organic electronics recent years. These species offer many advantages as potential replacement for conventional (i.e., silicon and metals) terms of cheap fabrication environmentally benign devices. While p-type (electron-donating or hole-conducting) been extensively reviewed researched, their counterpart n-type (electron-accepting electron-conducting) seen less popularity despite the greater need improvement. In...

In this account, we describe our efforts in developing the chemistry of highly luminescent dithieno[3,2-<i>b</i>:2′,3′-<i>d</i>]phosphole system over last ten years. We provide an overview synthetic possibilities and inherent tunability emission properties offered by particular heterole. 1 Introduction 2 Synthesis Properties Dithieno[3,2-<i>b</i>:2′,3′-<i>d</i>]phospholes 3 Functionalization 3.1 Phosphorus 3.2 at 2- 6-Positions 3.2.1 Symmetric 3.2.2 Asymmetric 3.3 Incorporation Fused Rings...