Photochromic benzo[b]phosphole oxide with excellent thermal irreversibility and fatigue resistance in the thin film solid state via direct attachment of dithienyl units to the weakly aromatic heterocycle

Abstract

Direct attachment of a photoactive bis-thienyl unit to benzo[b]phosphole oxide has led to a new photochromic compound that shows excellent performance in ambient thin film conditions.

Intramolecular Phosphacyclization: Polyaromatic Phosphonium P‐Heterocycles with Wide‐Tuning Optical Properties

“…Because of this distortion, phosphacyclic motifs feature a boat‐like conformation, which is reminiscent to the configuration of a family of acridophosphine compounds, but it is not observed in the planar systems based on the naphthalene moiety . The C−P bond lengths in 1 c , 2 c , and 4 c are in the range 1.765(2)–1.796(1) Å; the observed parameters are typical for P heterocyclic compounds with λ 5 ‐σ 4 or λ 4 ‐σ 4 phosphorus centers, such as phosphole oxides, phospha‐fluorescein, and related derivatives including cyclic phosphonium salts …”

Photoswitching of Copper(I) Chromophores with Dithienylethene‐Based Ligands

“…In these compounds, the thienyl groups are attached to five‐ or six‐membered rings such as the cyclopentene moiety to prevent unwanted cis ‐ trans isomerization. Most modifications of this basic motif have involved changes to the thienyl units, but now significant efforts have been extended to replace the five‐membered ring systems with various heterocycles . Yam and co‐workers in 2004 first reported 1,10‐phenanthroline functionalized dithienylethene as a ligand for metal coordination .…”

“…[10][11][12][13][14][15][16][17] Yam and co-workers in 2004 first reported 1,10-phenanthroline functionalizedd ithienylethene as al igand for metalc oordination. In these compounds, the thienyl groups are attached to five-or six-memberedr ings such as the cyclopentene moiety to prevent unwanted cis-trans isomerization.M ost modificationso f this basic motif have involvedc hanges to the thienylu nits, but now significant efforts have been extended to replacet he fivemembered ring systems with various heterocycles.…”

“…In these compounds, the thienyl groups are attached to five-or six-memberedr ings such as the cyclopentene moiety to prevent unwanted cis-trans isomerization.M ost modificationso f this basic motif have involvedc hanges to the thienylu nits, but now significant efforts have been extended to replacet he fivemembered ring systems with various heterocycles. [10][11][12][13][14][15][16][17] Yam and co-workers in 2004 first reported 1,10-phenanthroline functionalizedd ithienylethene as al igand for metalc oordination. [16] Since then, there have been extensivee fforts to coordinate metals including Ru, Re, Pt, Zn, Au, Pd, Fe, and Eu [9,[18][19][20] to dithienylethene-based ligands.…”

Synthesis of benzo[b]phosphole‐based alkynylgold(I) complexes with resistive memory properties modulated by donor–acceptor chromophores

“…On the other hand, phosphole, being an organic molecular compound or as a ligand for coordination to various transition metal centers, has received increasing research interests in the past decade 14,44–60 . Desirable properties, such as tunable electrochemical characteristics, facile molecular functionalization and intermolecular packing have been observed in various classes of phosphole moieties, allowing the design of smart materials in the fields of organic electronics, 14,52,59,60 photochromism, 44,54 chemosensing, 50,51,56 and supramolecular chemistry 48,53,55,57 .…”