Third-order Nonlinear Optical Properties of Organoboron Compounds: Molecular Structures and Second Hyperpolarizabilities

Zheng, Yujun; Taylor, Nicholas J.; Ramachandran, Ravi P.; Marder, Todd B.

doi:10.1002/(sici)1099-0739(199604)10:3/4<305::aid-aoc463>3.0.co;2-g

Cited by 166 publications

(79 citation statements)

References 32 publications

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“…The boron atom is three-coordinate in an approximately trigonal planar geometry ( C-B-C angles = 359.43 • ). The C(9)-C(8)-B(1) angle is 125.24 (17) • . The angle between the mean plane defined by boron and its neighboring carbon atoms and the quinoline mean plane is approximately 49 • ( Table 1).…”

Section: Methodsmentioning

confidence: 99%

Reactivity of the Bifunctional Ambiphilic Molecule 8-(dimesitylboryl)quinoline: Hydrolysis and Coordination to CuI, AgI and PdII

2010

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The ambiphilic molecule 8-(dimesitylboryl)quinoline (1) was synthesized by treatment of 8-bromoquinoline or 8-iodoquinoline with n-BuLi followed by dimesitylboronfluoride. Hydrolysis of 1 is unusually rapid compared to bulky triorganoboranes with the sequential loss of mesitylene and formation of mesityl(quinolin-8-yl)borinic acid (2) and 8-quinoline boronic acid dimer (3). Cooperativity within the bifunctional ambiphilic site leads to water activation and protodeboronation of the B-C(Mes) bonds. Blocking of the ambiphilic site of 1 by methylation of the quinoline nitrogen atom leads to an air-stable N-methyl-quinolinium salt. Coordination complexes were formed by reaction of 1 with CuCl, Ag(OTf), and PdCl(2)(PhCN)(2) with coordination of the quinolinyl nitrogen to the metal ion. The Cu(I) and Ag(I) centers are stabilized by η(3)-BC(ipso)C(ortho)π-interaction. The isolated Pd(II) complex is a product of cyclometalation, resulting from elimination of HCl upon deprotonation of the ortho-methyl group of nearby mesityl. The bonding in 7 could be understood as a 16-electron Pd complex that features an anionic η(3)-C(ipso)-C(ortho)-C(benzyl) allylic ligand fragment plus a Pd→B bond, or an η(4)-BC(ipso)-C(ortho)-C(benzyl) boratabutadiene anion fragment.

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Section: Methodsmentioning

confidence: 99%

Reactivity of the Bifunctional Ambiphilic Molecule 8-(dimesitylboryl)quinoline: Hydrolysis and Coordination to CuI, AgI and PdII

2010

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“…Fluorescent colors in both solvents changed from blue to blue-greenish. Solvent-dependent emission had been frequently observed for three-coordinate organoboron compounds and had been attributed to the presence of a highly polarized excited state [35][36][37] .…”

Section: Optical Propertiesmentioning

confidence: 99%

Synthesis and light-emitting properties of 2-(N-phenyl-α-naphthylamino) and 2-dimesitylboron-7-(N-phenyl-α-naphthylamino)-9,9-diethylfluorene

Zhang

Hui

et al. 2009

Sci. China Ser. B-Chem.

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A fluorescent organic triarylamine with a symmetric structure, 2,7-bis(N-α-naphthyl-phenylamino)-9,9-diethylfluorene (NPAEF) was synthesized using two methods, modified Ullmann coupling and modified palladium-catalyzed amination. An activated copper and a combination of Pd(OAc) 2 /P(t-Bu) 3 and Pd(dba) 2 /P(t-Bu) 3 were selected as catalysts to improve yields of reactions. These synthetic procedures were also successfully applied to an asymmetric 2-dimesitylboron-7-(N-phenyl-α-naphthylamino)-9,9-diethylfluorene (BNPEF). Photoluminescent emission peaks in solid film and in diluted solution of NPAEF were both observed at 461 nm, while the main emission peaks of BNPEF appeared at 422 nm in hexane, and at 480 nm in methanol. The double emission peaks of BNPEF in hexane reflected fine structure in the vibrational state. With an increasing polarity of solvent, the main PL emission peaks were red-shifted and vibrational fine structure disappeared. Additionally, energy levels of NPAEF were investigated and an electroluminescence (EL) device of ITO/PVK:NPAEF/Al was fabricated, which showed a turn-on voltage of 9 V and peaked at 462 nm. The EL spectrum was in good agreement with PL spectrum, which indicated that they were from the same emitting center in the device.

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“…It has been demonstrated that this kind of material can be used in a range of fields, such as nonlinear optics (NLO) [1][2][3][4], two-photon absorption (TPA) and emission materials [5][6][7][8][9], electron-transporting and emissive materials in organic light-emitting teleportation materials as well as chemosensors.…”

Section: Introductionmentioning

confidence: 99%

“…However, most of these do not give sufficient steric protection to the boron centre to render it stable in air [12][13][14][15][16]. Marder et al prepared three compounds using phenyl (1), 4-(1,1-Dimethylethyl) phenol (2) and 4-N,N-diphenylaminophenyl (3) groups attached to bis(fluoromesityl)boryl ((FMes)2B) by B-C bonds [17].…”

Section: Introductionmentioning

confidence: 99%

“…In this paper, we studied the influence of alternative acceptor groups bis(fluoromesityl) boryl((FMes) 2 B, FMes= fluoromesityl = 2,4,6-tris(trifluoromethyl) phenyl), which is an analogue of (Mes) 2 B with the methyl groups replaced by CF 3 oxidation groups [18], under different conditions: in vacuum, in the nonpolar solvents Hexane and Toluene, and in the polar solvents THF and CH 3 CN. By using 3D real-space analysis [19][20][21][22][23][24], we studied the properties of charge and energy transfer, transition of the dipole moment, electron-hole coherence and delocalization of compounds in different solvents at excited states.…”

Section: Introductionmentioning

confidence: 99%

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Optical and electronic properties of organoboron compounds in solvent

Shan¹

2017

JAMS

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Abstract. Organoboron compounds 1-4 with an aryl ring directly bound to a (FMes) 2 B group through B-C bonds in vacuum, Hexane, Toluene, THF, CH 3 CN were theoretically studied using DFT with B3LYP functional and 6-31G (d) basis set, and TD-DFT with CAM-B3LYP functional and 6-31G (d) basis set. The absorption and fluorescence spectra of compounds 1-4 are determined in the same and different solvents. It is found that the electronic transition is the most efficient when compounds 1-4 are in CH 3 CN, the most polar solvent. The spectral contrast of compounds 3 and 4 is studied under different conditions. The charge difference density (CDD) is determined using the data from the intramolecular charge transfer of compounds 1-4 using 3D cube with large oscillator strength.

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Third-order Nonlinear Optical Properties of Organoboron Compounds: Molecular Structures and Second Hyperpolarizabilities

Cited by 166 publications

References 32 publications

Reactivity of the Bifunctional Ambiphilic Molecule 8-(dimesitylboryl)quinoline: Hydrolysis and Coordination to CuI, AgI and PdII

Reactivity of the Bifunctional Ambiphilic Molecule 8-(dimesitylboryl)quinoline: Hydrolysis and Coordination to CuI, AgI and PdII

Synthesis and light-emitting properties of 2-(N-phenyl-α-naphthylamino) and 2-dimesitylboron-7-(N-phenyl-α-naphthylamino)-9,9-diethylfluorene

Optical and electronic properties of organoboron compounds in solvent

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