p -Carborane Conjugation in Radical Anions of Cage–Cage and Cage–Phenyl Compounds

Cook, Andrew R.; Valášek, Michal; Funston, Alison M.; Poliakov, Pavel; Michl, Josef; Miller, John R.

doi:10.1021/acs.jpca.7b10885

Title: p -Carborane Conjugation in Radical Anions of Cage–Cage and Cage–Phenyl Compounds

Journal Article · Thu Dec 14 00:00:00 EST 2017 · Journal of Physical Chemistry. A, Molecules, Spectroscopy, Kinetics, Environment, and General Theory

DOI:https://doi.org/10.1021/acs.jpca.7b10885· OSTI ID:1425003

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^[3]; Poliakov, Pavel ^[1]; Michl, Josef ^[4];

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Brookhaven National Lab. (BNL), Upton, NY (United States). Chemistry Dept.
Academy of Sciences of the Czech Republic (ASCR), Prague (Czech Republic). Inst. of Organic Chemistry and Biochemistry
Brookhaven National Lab. (BNL), Upton, NY (United States). Chemistry Dept.; Monash Univ., Victoria (Australia). School of Chemistry
Academy of Sciences of the Czech Republic (ASCR), Prague (Czech Republic). Inst. of Organic Chemistry and Biochemistry; Univ. of Colorado, Boulder, CO (United States). Dept. of Chemistry and Biochemistry

Optical electron transfer (intervalence) transitions in radical anions of p-carborane oligomers attest to delocalization of electrons between two p-carboranes cages or a p-carborane and a phenyl ring. Oligomers of the 12 vertex p-carborane (C₂B₁₀H₁₂) cage, [12], with up to 3 cages were synthesized, as well as p-carboranes with one or two trimethylsilylphenyl groups, [6], attached to the carbon termini. Pulse radiolysis in tetrahydrofuran produced radical anions, determined redox potentials by equilibria and measured their absorption spectra. Density functional theory computations provided critical insight into the optical electron transfer bands and electron delocalization. One case, [6–12–6], showed both Robin–Day class II and III transitions. The class III transition resulted from a fully delocalized excess electron across both benzene rings and the central p-carborane, with an electronic coupling H_ab = 0.46 eV between the cage and either benzene. This unprecedented finding shows that p-carborane bridges are not simply electron withdrawing insulators. In other cases with more than ~1/2 of the excess electron localized on a [12], large cage distortions were triggered, producing a partially open cage with a nido-like structure. This resulted in class II transitions with similar Hab but massive reorganization energies. The computations also predicted delocalization in radical cations, but complexities in cation formation allowed only tentative experimental support of the predictions. Thus, the results with anions provide clear evidence for carborane conjugation that might be exploited in molecular wire materials, which are classically composed of all π-conjugated molecules.

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Research Organization:: Brookhaven National Laboratory (BNL), Upton, NY (United States)

Sponsoring Organization:: USDOE Office of Science (SC), Basic Energy Sciences (BES). Chemical Sciences, Geosciences, and Biosciences Division; National Science Foundation (NSF); Academy of Sciences of the Czech Republic (ASCR), Prague (Czech Republic). Inst. of Organic Chemistry and Biochemistry

Grant/Contract Number:: SC0012704; CHE 1566435; 61388963

OSTI ID:: 1425003

Report Number(s):: BNL-114846-2017-JAAM; TRN: US1801995

Journal Information:: Journal of Physical Chemistry. A, Molecules, Spectroscopy, Kinetics, Environment, and General Theory, Vol. 122, Issue 3; ISSN 1089-5639

Publisher:: American Chemical SocietyCopyright Statement

Country of Publication:: United States

Language:: English

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Cited by: 9 works

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Metal—lingad and metal—metal coupling elements Creutz, Carol; Newton, Marshall D.; Sutin, Norman Journal of Photochemistry and Photobiology A: Chemistry, Vol. 82, Issue 1-3 https://doi.org/10.1016/1010-6030(94)02013-2	journal	August 1994
Two-dimensional potential surfaces for bridged mixed-valence dimers Ondrechen, Mary Jo; Ko, Jaeju; Root, Leslie J. The Journal of Physical Chemistry, Vol. 88, Issue 24 https://doi.org/10.1021/j150668a034	journal	November 1984
Ab initio quantum chemical study of electron transfer in carboranes Pati, Ranjit; Pineda, Andrew C.; Pandey, Ravindra Chemical Physics Letters, Vol. 406, Issue 4-6 https://doi.org/10.1016/j.cplett.2005.03.039	journal	May 2005

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Dinuclear acetylide-bridged ruthenium( ii ) complexes with rigid non-aromatic spacers Naik, Surabhi; Scottwell, Synøve Ø.; Li, Hsiu L. Dalton Transactions, Vol. 49, Issue 8 https://doi.org/10.1039/c9dt04856a	journal	January 2020

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