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Empty Level Structure of Boryl-Substituted Pentacyclic Heteroaromatics

Empty Level Structure of Boryl-Substituted Pentacyclic Heteroaromatics

Alberto Modelli, Derek Jones

Phys Chem Chem Phys. 2011 Jan 7;13(1):276-81.

PMID: 21088783

Abstract:

Extended π-conjugation in molecular systems is being extensively exploited in a rapidly expanding range of electronic and photonic applications. The modification of such extended systems through the use of heteroatoms allows their tailoring to specific requirements. In particular, the use of the vacant boron p(π) orbital can increase the electron affinity of the extended π system in an analogous fashion to the p-doping of crystalline silicon used in more classical microelectronic devices. Experimental data on such modifications of the empty level structures of boron-containing π-electron materials leading to an increase in their electron affinity are not available in the literature. Using Electron Transmission Spectroscopy, the energies of the vertical anion formation of 5-methyl-2-furanboronic acid pinacol ester (1) and 4-methyl-3-thiopheneboronic acid pinacol ester (2) are measured and compared with those of the reference unsubstituted heteroaromatics furan and thiophene. The results are interpreted with the support of density functional theory (DFT) calculations with the B3LYP functional. DFT calculations are also used to predict the effects of boryl substituents on the electronic and geometrical structures of trans and cis thienyl thiazole.

Chemicals Related in the Paper:

Catalog Number	Product Name	CAS Number	Price
AP476620209	4-Methyl-3-thiopheneboronic acid pinacol ester	476620-20-9	Price
AP62306790	5-Methyl-2-furanboronic acid	62306-79-0	Price
AP849061990	(trans)-2-Cyclopropylvinylboronic acid pinacol ester	849061-99-0	Price
LS793421	methyl 3-amino-5-boronobenzoate, pinacol ester		Price

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