Synthesis of water-soluble subphthalocyanines

Łapok, Łukasz; Claessens, Christian G.; Wöhrle, Dieter; Torres, Tomás

doi:10.1016/j.tetlet.2009.02.066

Cited by 31 publications

(21 citation statements)

References 28 publications

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“…Approaches to creating water-soluble BsubPcs also exist and generally involve the formation of a water-soluble salt. 112 Sublimability is also of concern. BsubPc derivatives with axial fluoro-, chloro-, methoxy-, and methyl-subsituents, and derivatives containing dodecafluoro and hexachloro peripheral substitutents have been reported as sublimable.…”

Section: ■ Materials Properties and Device Performancementioning

confidence: 99%

Boron Subphthalocyanines as Organic Electronic Materials

Morse

Bender

2012

ACS Appl. Mater. Interfaces

205

181

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Boron subphthalocyanines (BsubPcs) are an emerging class of high performing materials in organic electronics. Since the first use of chloroboron subphthalocyanine in an organic electronic device 6 years ago subphthalocyanines have shown potential as functional materials in organic light emitting diodes (OLEDs) and organic photovoltaics (OPVs). Here we review the material properties of chloroboron subphthalocyanine (Cl-BsubPc) and its use as an organic semiconductor. We then highlight our efforts toward derivatives of boron subpthalocyanine beyond Cl-BsubPc and discuss the impact of molecular design on the material properties and the performance of the BsubPc. Finally, we comment on the status of BsubPcs in the field of organic electronics and discuss how we believe future progress can be made.

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Section: ■ Materials Properties and Device Performancementioning

confidence: 99%

Boron Subphthalocyanines as Organic Electronic Materials

Morse

Bender

2012

ACS Appl. Mater. Interfaces

205

181

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“…This rare example of a non‐planar, bowl‐shaped, fourteen π‐electron aromatic system was first reported in 1972 by Meller and Ossko as a product formed during an unsuccessful attempt to prepare a boron phthalocyanine . Three iminoisoindole subunits N‐fused around a boron atom and a halogen atom at the axial position form a subphthalocyanine macrocycle . The recent surge of interest in this class of compounds stems from their unique and tunable optical and electrochemical properties, such as strong absorption of light in the visible part of the spectrum, tunable HOMO/LUMO energy levels, and triplet‐state characteristics.…”

Section: Introductionmentioning

confidence: 99%

Facile Synthesis, Triplet‐State Properties, and Electrochemistry of Hexaiodo‐Subphthalocyanine

Obłoza

Łapok

Solarski

et al. 2018

Chemistry A European J

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In view of the ever-growing demand for efficient triplet photosensitizers and photoactive components of various optoelectronic devices, we herein report the synthesis and properties of hexaiodo-subphthalocyanines (I SubPcs). The improved five-step route to 4,5-diiodophthalonitrile, which serves as precursor for the synthesis of the I SubPcs, is reported. The improved synthesis merely required one chromatographic separation to afford the high-purity target product. Highly desirable photophysical and photochemical properties were induced in the I SubPcs due to the presence of six heavy iodine atoms. In particular, high values of the singlet-oxygen quantum yields (Φ ) ranging from 0.83 to 0.9 were measured. The I SubPcs investigated proved to be phosphorescent at 77 K in 2-MeTHF with emission band maxima (λ ) located at λ=957 and 970 nm. The excited-triplet-state energies (E ) were estimated to be approximately 1.30 eV, whereas the triplet lifetimes (τ ) were found to be 27.7 and 30.1 μs. The CV/DPV measurements indicated that both I SubPcs exhibited one irreversible oxidation and one quasi-reversible reduction. The spectroelectrochemical measurements pointed to a relative stability and reversibility of the electrochemically formed anion radical, that is, I SubPc , and an instability of the species formed upon one-electron oxidation, that is, I SubPc . Estimation of E gave a value of approximately -5.8 eV whereas E was found to be located at around -3.8 eV.

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“…Minimized geometry-optimized structures were first performed at the semi-empirical level (PM6 method), followed by energy-minimized DFT calculations at the B3LYP level (basis sets:6 -31G*) to compute the molecular frontier orbitals. TriiodoSubPc (7), [23] 4-octylsulfonylphthalonitrile (14) [26] 4'-(4-tertbutlyphenylthio) phthalonitrile (15), [27] 4-octylthiophthalonitrile (16), dibenzo[b,e] [1,4]dioxine-2,3-dicarbonitrile (17), [3] 4-iodophthalonitrile (18), [28,29] 4-ethynylbenzoic acid, [22] and 4-ethynylbenzaldehyde [30] were prepared according to procedures previously reported in the literature.…”

Section: Methodsmentioning

confidence: 99%

“…In recent years, research based on subphthalocyanines (SubPcs) [1] has attracted great attentiono wing to their fundamental scientific importance and utility in aw ide range of applicationsi nf ields such as nonlinear optics, [2,3] OLEDs, [4,5] photodynamic therapy, [6][7][8] and photo-electroactive systems. [9][10][11][12] They have received considerable interesta sa na lternative active layer component in photovoltaic devices due to their strong absorption in the visible region (500-700 nm), low oxidation potential, and high electron mobility.…”

Section: Introductionmentioning

confidence: 99%