Thermal stability of boron subphthalocyanines as a function of the axial and peripheral substitution

González‐Rodríguez, David; Torres, Tomás; Denardin, Elton Luís Gasparotto; Samios, Dimitrios; Stéfani, Valter; Corrêa, Dione Silva

doi:10.1016/j.jorganchem.2008.10.055

Cited by 25 publications

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References 43 publications

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“…[14] SubPc-Pnc 2 s 4-6 were prepared by an axial substitution reaction starting with the corresponding chloro-precursors via the generation of aSubPc-triflate intermediate,following aprocedure reported by us (Figure 1a nd Supporting Information). [14] SubPc-Pnc 2 s 4-6 were prepared by an axial substitution reaction starting with the corresponding chloro-precursors via the generation of aSubPc-triflate intermediate,following aprocedure reported by us (Figure 1a nd Supporting Information).…”

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“…Syntheses of SubPcs 1-3 have been described in the literature and were carried out accordingly. [14] SubPc-Pnc 2 s 4-6 were prepared by an axial substitution reaction starting with the corresponding chloro-precursors via the generation of aSubPc-triflate intermediate,following aprocedure reported by us ( Figure 1a nd Supporting Information). [15] Pnc 2 7 was prepared according to ar ecently described procedure.…”

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Tuning Intramolecular Förster Resonance Energy Transfer and Activating Intramolecular Singlet Fission

et al. 2018

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The synergy of panchromatic absorption throughout most of the visible range of the solar spectrum and intramolecular singlet fission (SF) has been realized in a series of conjugates featuring different light-harvesting subphthalocyanines (SubPcs) and an energy accepting pentacene dimer (Pnc ). At the focal point was a modular SubPc approach, which was based on decorating the SubPc core with different peripheral substituents to tailor and fine-tune their optical properties. Transient absorption measurements assisted in corroborating that the SubPcs act as energy-transfer antennas by means of unidirectional and quantitative intramolecular Förster resonance energy transfer (FRET) to the Pnc , where an intramolecular SF affords triplet quantum yields reaching unity.

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Tuning Intramolecular Förster Resonance Energy Transfer and Activating Intramolecular Singlet Fission

et al. 2018

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“…Boron subphthalocyanines (SubPcs) have similar physico-chemical properties to phthalocyanine: a delocalized 14π electron system, good chemical and thermal stability, one-step synthesis route, simple purification, conducive to industrialization. SubPcs also have high modification and can obtain different optoelectronic properties by modifying different groups in the α, β position or on the central B atom to meet the needs of different optoelectronic devices [ 33 – 41 ]. However, SubPc also has a poor organic solubility (similar to Pc) and its HOMO level is too low to align with the valence band of the perovskite material, which limits its potential application in PSCs [ 42 ].…”

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Soluble hexamethyl-substituted subphthalocyanine as a dopant-free hole transport material for planar perovskite solar cells

Wang¹,

Liu²,

Rezaee³

et al. 2018

R. Soc. open sci.

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Boron subphthalocyanine (SubPc) has special physical and chemical properties, originating from its non-centrosymmetric, near-planar taper structure and large conjugated system; it can act as an alternative to the small molecule hole-transporting material 2,2′,7,7′-tetrakis-(N,N-di-p-methoxyphenylamine)-9,9′-spirobifluorene in perovskite solar cells (PSCs). To achieve a higher solubility in common organic solvents and a more suitable highest occupied molecular orbital energy level that aligns with the valence band of the perovskite material, a SubPc molecule with a hexamethyl substitution at its peripheral position (Me6-SubPc) was successfully designed and synthesized in a one-step method. Completely solution processed PSCs were fabricated with only a small hysteresis, a power conversion efficiency of 6.96% and Voc of 0.986 V.

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“…[14] SubPc-Pnc 2 s 4-6 wurden mithilfe einer axialen Substitutionsreaktion hergestellt. [14] SubPc-Pnc 2 s 4-6 wurden mithilfe einer axialen Substitutionsreaktion hergestellt.…”

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“…Die Synthesen der SubPcs 1-3 wurden bereits beschrieben und dementsprechend durchgeführt. [14] SubPc-Pnc 2 s 4-6 wurden mithilfe einer axialen Substitutionsreaktion hergestellt. Dabei starteten wir mit den entsprechenden Chlorvorstufen über die Bildung einer SubPc-Triflat-Zwischenstufe gemäßeiner bereits von uns publizierten Route [Abbildung 1 und Hintergrundinformationen (SI)].…”

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Feinabstimmung von intramolekularem resonantem Förster‐Energietransfer und Aktivierung intramolekularer Singulettspaltung

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Die Synergie panchromatischer Lichtabsorption, die einen Großteil des sichtbaren Sonnenspektrums abdeckt,sowie intramolekularer Singulettspaltung (singlet fission, SF) wurde in einer Serie von Konjugaten realisiert, die sich aus verschiedenen lichtsammelnden Subphthalocyaninen (SubPcs) und einem Pentacendimer (Pnc 2 )a ls Energieakzeptor zusammensetzte.ImF okus stand dabei ein Baukastenprinzip,das darauf basierte,d en SubPc-Kern in dessen Peripherie mit unterschiedlichen Substituenten zu funktionalisieren und damit die optischen Eigenschaften feinabzustimmen. Transiente Absorptionsstudien halfen dabei zu bestätigen, dass die SubPcs mittels eines gerichteten quantitativen resonanten Fçrster-Energietransfers (Fçrster resonance energy transfer,F RET) zum Pnc 2 als Antennen füre inen Energietransfer fungierten. Im Pnc 2 wurden anschließend mittels intramolekularer SF nahezu quantitative Triplettquantenausbeuten erzielt.

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Thermal stability of boron subphthalocyanines as a function of the axial and peripheral substitution

Cited by 25 publications

References 43 publications

Tuning Intramolecular Förster Resonance Energy Transfer and Activating Intramolecular Singlet Fission

Tuning Intramolecular Förster Resonance Energy Transfer and Activating Intramolecular Singlet Fission

Soluble hexamethyl-substituted subphthalocyanine as a dopant-free hole transport material for planar perovskite solar cells

Feinabstimmung von intramolekularem resonantem Förster‐Energietransfer und Aktivierung intramolekularer Singulettspaltung

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