Synthesis and photophysical properties of imine borane adducts towards vapochromic materials

Soltani, Yashar; Adams, Samuel J.; Börger, Jennifer; Wilkins, Lewis C.; Newman, Paul D.; Pope, Simon J. A.; Melen, Rebecca L.

doi:10.1039/c8dt03019g

Cited by 16 publications

(8 citation statements)

References 28 publications

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“…26 Furthermore, in this context, Romero-Nieto and Hashmi have shown that the LA B(C 6 F 5 ) 3 can coordinate to the oxygen center of conjugated aldehydes to trigger strong luminescence, even in the solid state, 27 whereas Melen and co-workers have used a similar concept in an attempt to establish such luminescent adducts as vapochromic sensors. 28 Herein, we introduce a simple and powerful, naked-eye litmus test for determining the strength of LAs via the use of fluorescent phosphole oxides, by generating fluorescent Lewis acid-base adducts (FLAs) with distinctly altered fluorescence and coloration properties. In this proof-of-concept study, we report the detailed fluorescence and chromaticity responses of the dithienophosphole system in the presence of a series of important LAs to showcase the available Lewis-acidity range for our method.…”

Section: Introductionmentioning

confidence: 99%

A Simple and Effective Method of Determining Lewis Acidity by Using Fluorescence

Gaffen

Bentley

Torres

et al. 2019

Chem

140

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Section: Introductionmentioning

confidence: 99%

A Simple and Effective Method of Determining Lewis Acidity by Using Fluorescence

Gaffen

Bentley

Torres

et al. 2019

Chem

140

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“…For Mn-III, the potential shifts anodically by 2.14 V upon coordination of BCF, while for 246, the anodic shift is 1.1 V, or approximately 350 mV for each coordinated BCF (AN = 77.15 -82) 93,94 and 180 mV for each coordinated 246 (AN = 68.5). 95,96 Considering all five M-III-BCF species, the potential shift increase tracks with the decrease in average M-C bond length (1.921 Å (Fe-III-BCF) < 1.99 Å (Mn-III-BCF) < 2.030 Å (Ru-III-BCF) < 2.055 Å (Os-III-BCF) < 2.065 Å (Cr-III-BCF)).…”

Section: Shifts In Formal Potentials For Boronated Cyanometallate Red...mentioning

confidence: 98%

Boronated Cyanometallates

McNicholas,

Nie,

Jose

et al. 2022

Preprint

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Fourteen boronated cyanometallates ([M(CN-BR3)6]3/4/5– (M = Cr, Mn, Fe, Ru, Os, R = BPh3, B(2,4,6,-F3C6H2)3, B(C6F5)3) have been characterized by X-ray crystallography and spectroscopy [UV-vis-NIR, NMR, IR, spectroelectrochemistry, and magnetic circular dichroism (MCD)]; CASSCF+NEVPT2 methods were employed in calculations of electronic structures. For (t2g)5 electronic configurations, the lowest energy ligand-to-metal charge transfer (LMCT) absorptions and MCD C terms in the spectra of boronated species have been assigned to transitions from cyanide σ+π + B-C borane σ orbitals. CASSCF+NEVPT2 calculations including t1u and t2u orbitals reproduced t1u/t2u → t2g excitation energies. All ([M(CN-BR3)6]3/4− complexes exhibited highly electrochemically reversible redox couples. Notably, the formal potentials of all five [M(CN-B(C6F5)3)6]3− anions scale with LMCT energies; and Mn(I) and Cr(II) compounds, (K(18-crown-6))5[Mn(CN-B(C6F5)3)6] and (TBA)4[Cr(CN-B(C6F5)3)6], are surprisingly stable. Continuous wave and pulsed electron paramagnetic resonance (hyperfine sublevel correlation) spectra were collected for all Cr(III) complexes; as expected, 14N hyperfine splittings are greater for (TBA)3[Cr(NC-BPh3)6] than for (TBA)3[Cr(CN-BPh3)6]. Using (TBA)4[Fe(CN-B(C6F5)3)6] and (TBA)3[Fe(CN)6], a model flow battery was constructed and found to have an 80% energy effi-ciency.

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“…[ 50 ] B←N complexation was also observed between the alkynyl aryl‐conjugated imine (14) and various B Lewis acids, e.g., BX 3 (X = F, Cl, and Br), BCF, and BPh 3 to shifted the absorption and fluorescence to lower energy. [ 51 ] Besides solid fluorescence, the crystallization fluorescence enhancement was also surveyed in the crystal of 15‐BCF complex. Crystallization‐induced emission enhancement in 15‐BCF was ascribed to the intermolecular C–H•••F interactions in the crystals, which may restrict the molecular motions and deactivate the nonradiative decay pathway.…”

Section: Intermolecular B←n Coordinationmentioning

confidence: 99%

B←N Coordination: From Chemistry to Organic Photovoltaic Materials

Huang

Wang

Xiang

et al. 2021

Adv Energy and Sustain Res

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Coordination between boron Lewis acid and nitrogen Lewis base (B←N) is a classically chemical issue that has been known for several decades. Recently, this B←N chemistry developed into a new stage toward electronic materials, e.g., adjusting optoelectronic properties of N‐based conjugated molecules via adding B Lewis acids, synthesizing B←N‐bridged conjugated units, and further constructing B←N‐embedded organic photovoltaic (OPV) materials. Herein, these progresses are systematically summarized starting from certain chemical issues concerning B←N coordination, e.g., Lewis acidity of typical B Lewis acids and their interactions with N‐contained conjugated molecules. Then, some fused and ladder‐type B←N‐bridged units are reviewed in terms of the relationship between molecular structures and optoelectronic properties. Finally, the recently flourished B←N‐embedded OPV materials are summarized. The prospect of OPV materials concerning B←N coordination is also proposed, hoping to attract more attention to this filed and motivate its rolling rapidly.

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Synthesis and photophysical properties of imine borane adducts towards vapochromic materials

Cited by 16 publications

References 28 publications

A Simple and Effective Method of Determining Lewis Acidity by Using Fluorescence

A Simple and Effective Method of Determining Lewis Acidity by Using Fluorescence

Boronated Cyanometallates

B←N Coordination: From Chemistry to Organic Photovoltaic Materials

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