This review focuses on classifying different types of long wavelength absorbing BODIPY dyes based on the wide range of structural modification methods that have been adopted, and on tabulating their spectral and photophysical properties. The structure–property relationships are analyzed in depth with reference to molecular modeling calculations, so that the effectiveness of the different structural modification strategies for shifting the main BODIPY spectral bands to longer wavelengths can be readily compared, along with their effects on the fluorescence quantum yield (ΦF) values. This should facilitate the future rational design of red/NIR region BODIPY dyes for a wide range of different applications.

Structural modification strategies for the rational design of red/NIR region BODIPYs

Multidisciplinary research on novel organic luminescent dyes is propelled by potential applications in plastic electronics and biomedical sciences. The construction of sophisticated fluorescent dyes around a tetrahedral boron(III) center is a particular approach that has fueled the creativity of chemists. Success in this enterprise has been readily achieved with simple synthetic protocols, the products of which display unusual spectroscopic behavior. This account is a critical review of recent advances in the field of boron(III) complexes (excluding BODIPYs and acetylacetonate boron complexes) involving species displaying similar coordination features, and we outline their potential development in several disciplines.

Luminescent materials: locking π-conjugated and heterocyclic ligands with boron(III).

Four-coordinate organoboron compounds with rigid π-conjugated structures are intensely luminescent and have high carrier mobility which enables them to be applied in optoelectronics including organic light-emitting diodes (OLEDs), organic field-effect transistors, as well as photoresponsive, sensory and imaging materials. Various chelate ligands and boron moieties have been explored to construct proper electronic structures and suitable molecular arrangements, which play important roles on the photophysical and electronic properties of the four coordinate boron compounds. These efforts have produced a number of fascinating molecules, some of which have exhibited high performance as light emitting materials. In this article, we provide an overview of the progress in the molecular construction of four-coordinate organoboron compounds with an emphasis on their applications in OLEDs.

Four-coordinate organoboron compounds for organic light-emitting diodes (OLEDs).

It is known that electron donating groups have quite a different effect on the π-delocalization of a conjugate system when bonded at ortho and para as compared to meta positions in the phenyl ring. In the present work, the BF2 complex of 1-phenyl-3-(3,5-dimethoxyphenyl)-propane-1,3-dione (1), a molecule with two methoxy groups in one of the phenyl rings at meta positions, was prepared. Compound 1 exists as two polymorphs having different mutual orientations of the two methoxy groups: in polymorph A away from each other (termed anti), while in polymorph B one methoxy group is oriented toward the other (syn–anti). In both crystals, the molecules which are antiparallel (the subPh rings as well as dioxaborine are on opposite sides) form stacks through face-to-face π–π interactions, while in polymorph A the crystal packing is further stabilized by intermolecular C(phenyl)–H···F and C(methoxy)–H···F hydrogen bonds. Solid A possesses numerous chromic effects, including mechano-, thermo-, and chronochromism, thou...

Crystal Structures and Emission Properties of the BF2 Complex 1-Phenyl-3-(3,5-dimethoxyphenyl)-propane-1,3-dione: Multiple Chromisms, Aggregation- or Crystallization-Induced Emission, and the Self-Assembly Effect

Four-coordinate organoboron compounds with a π-conjugated chelate backbone have emerged recently as highly attractive materials for a number of applications including use as emitters and electron-transport materials for organic light-emitting diodes (OLEDs) or organic field transistors, photoresponsive materials, and sensory and imaging materials. Many applications of this class of boron compounds stem from the electronic properties of the π-conjugated chelate backbone. Charge-transfer transitions from an aromatic substituent attached to the boron center of the π-conjugated chelate backbone and steric congestion have also been found to play important roles in the luminescent and photochromic properties of the four-coordinate boron compounds. This article provides an update-to-date account on the application aspects of this important class of compounds in materials science with the emphasis on OLED applications and photochromic switching.

Four-Coordinate Organoboron Compounds with a π-Conjugated Chelate Ligand for Optoelectronic Applications

Four diboron-contained ladder-type π-conjugated compounds 1−4 were designed and synthesized. Their thermal, photophysical, electrochemical properties, as well as density functional theory calculations, were fully investigated. The single crystals of compounds 1 and 3 were grown, and their crystal structures were determined by X-ray diffraction analysis. Both compounds have a ladder-type π-conjugated framework. Compounds 1 and 2 possess high thermal stabilities, moderate solid-state fluorescence quantum yields, as well as stable redox properties, indicating that they are possible candidates for emitters and charge-transporting materials in electroluminescent (EL) devices. The double-layer device with the configuration of [ITO/NPB (40 nm)/1 or 2 (70 nm)/LiF (0.5 nm)/Al (200 nm)] exhibited good EL performance with the maximum brightness exceeding 8000 cd/m2.

Luminescent boron-contained ladder-type pi-conjugated compounds.

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Luminescent boron-contained ladder-type pi-conjugated compounds.