BOPHYs versus BODIPYs: A comparison of their performance as effective multi-function organic dyes

Sola-Llano, Rebeca; Jiménez, Josué; Avellanal‐Zaballa, Edurne; Johnson, M. R.; Cabreros, Trevor A.; Moreno, Florencio; Maroto, Beatriz Lora; Muller, Gilles; Bañuelos, Jorge; Cerdán, Luis; García‐Moreno, Inmaculada; Cerero, Santiago de la Moya

doi:10.1016/j.dyepig.2019.107662

Cited by 22 publications

(12 citation statements)

References 50 publications

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“…The structure of BOPHY dye 2 ( Figure 2) keeps the C2-symmetry of 1, but duplicates the number of BINOL moieties. Dyes 1 [16] and 2 [17] have been reported before by us and show maximum glum values of −0.6 × 10 −3 and −1.4 × 10 −3 , respectively, in the visible region upon visible irradiation (Table 1). These glum values are in the typical range for CPL-SOMs [7].…”

Section: Resultssupporting

confidence: 72%

Insight into the Influence of the Chiral Molecular Symmetry on the Chiroptics of Fluorescent BINOL-Based Boron Chelates

Jiménez

Avellanal‐Zaballa

Serrano

et al. 2020

The 24th International Electronic Conference on Synthetic Organic Chemistry

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The prominent influence of the molecular symmetry, as defined by the symmetry point group, on the chiroptical behavior (electronic circular dichroism and, especially, circularly polarized luminescence) of simple fluorescent boron chelates (BODIPY and related BOPHY analogues) is studied and discussed. It is shown that increasing the dye symmetry by means of the D3 chiral symmetry group is a workable design option to enhance the level of differential emission of rightand left-circularly polarized light in BODIPY dyes and related emitters. And that the influence of the level of symmetry is stronger than the influence of the higher number of chiral moieties perturbing the acting achiral chromophore.

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Section: Resultssupporting

confidence: 72%

Insight into the Influence of the Chiral Molecular Symmetry on the Chiroptics of Fluorescent BINOL-Based Boron Chelates

Jiménez

Avellanal‐Zaballa

Serrano

et al. 2020

The 24th International Electronic Conference on Synthetic Organic Chemistry

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“…Am ore common method [55] for preparationo f chiral BODIPYs is to introduce ac hiral perturber in the vicinity of the boron atom [13] and resolve the mixture of diastereoisomers. Chiral BOPHY derivatives have been reported [56] wherein the fluorine atoms are replaced by enantiopure binaphthols, endowing the chromophore with chiroptical activity.T his strategy,h owever,l eads to am arked decrease in fluorescenceb ecause of the introductiono fa ni ntramolecular charge-transfer state. Chiral BORANILs have been synthesized from chiral benzylamines.…”

Section: Circular Dichroismmentioning

confidence: 99%

Synthesis, Structure and Photophysical Properties of a New Class of Inherently Chiral Boron(III) Chelates—The tert‐Leucine Complexes

Algoazy

Knight

Waddell

et al. 2021

Chemistry A European J

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A new family of boron(III) chelates is introduced whereby molecular chirality, confirmed by circular dichroism, is imported during synthesis such that isolation of the diastereoisomers does not require separation procedures. The photophysical properties of two members of the family have been examined: the N,O,O‐salicylaldehyde‐based derivative shows pronounced intramolecular charge‐transfer character in fluid solution and is weakly fluorescent, with a large Stokes shift. The corresponding 2‐methylamino‐benzaldehyde‐derived N,N,O‐chelate absorbs and fluoresces in the visible region with a much smaller Stokes shift. Orange fluorescence is also observed for this compound as a cast film. Temperature‐dependence studies show that decay of the fluorescent state is weakly activated but emission is less than quantitative at 77 K. Quite rare for boron(III)‐based chelates, this derivative undergoes intersystem crossing to form a meta‐stable triplet‐excited state. X‐ray crystal structures are reported for both compounds, along with simulated ECD spectra.

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“…In both dyes, the synthetic access involves boron chelation of a π‐conjugated pyrrole‐based system, but, in the BOPHY case, it includes a central hydrazine‐based spacer. [ 31,32 ] BOPHY dyes have been proven to be excellent photoactive materials suitable for several applications. In fact, we have reported the synthesis of BOPHY‐based CPPs as photocatalysts for oxidation of organic sulfides, [ 33 ] hydrogen production, [ 34 ] and also as part of a photon upconversion system.…”

Section: Introductionmentioning

confidence: 99%

Conjugated Porous Polymers Based on BODIPY and BOPHY Dyes in Hybrid Heterojunctions for Artificial Photosynthesis

Collado

Naranjo

Gomez‐Mendoza

et al. 2021

Adv Funct Materials

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Developing highly efficient photocatalysts for artificial photosynthesis is one of the grand challenges in solar energy conversion. Among advanced photoactive materials, conjugated porous polymers (CPPs) possess a powerful combination of high surface areas, intrinsic porosity, cross‐linked nature, and fully π‐conjugated electronic systems. Here, based on these fascinating properties, organic–inorganic hybrid heterostructures composed of CPPs and TiO2 for the photocatalytic CO2 reduction and H2 evolution from water are developed. The study is focused on CPPs based on the boron dipyrromethene (BODIPY) and boron pyrrol hydrazine (BOPHY) families of compounds. It is shown that hybrid photocatalysts are active for the conversion of CO2 mainly into CH4 and CO, with CH4 production 4 times over the benchmark TiO2. Hydrogen evolution from water surpassed by 37.9‐times that of TiO2, reaching 200 mmol gcat−1 and photonic efficiency of 20.4% in the presence of Pt co‐catalyst (1 wt% Pt). Advanced photophysical studies, based on time‐resolved photoluminescence and transient absorption spectroscopy, reveal the creation of a type II heterojunction in the hybrids. The unique interfacial interaction between CPPs and TiO2 results in longer carriers’ lifetimes and a higher driving force for electron transfer, opening the door to a new generation of photocatalysts for artificial photosynthesis.

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BOPHYs versus BODIPYs: A comparison of their performance as effective multi-function organic dyes

Cited by 22 publications

References 50 publications

Insight into the Influence of the Chiral Molecular Symmetry on the Chiroptics of Fluorescent BINOL-Based Boron Chelates

Insight into the Influence of the Chiral Molecular Symmetry on the Chiroptics of Fluorescent BINOL-Based Boron Chelates

Synthesis, Structure and Photophysical Properties of a New Class of Inherently Chiral Boron(III) Chelates—The tert‐Leucine Complexes

Conjugated Porous Polymers Based on BODIPY and BOPHY Dyes in Hybrid Heterojunctions for Artificial Photosynthesis

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