Preparation and Solid-State Structural, Electronic, and Magnetic Properties of the 5-Cyano-1,3-benzene-Bridged Bis(1,2,3,5-dithiadiazolyl) and Bis(1,2,3,5-diselenadiazolyl) [5-CN-1,3-C6H3(CN2E2)2] (E = S, Se)

A. W. Cordes, R. C. Haddon, R. G. Hicks, D. K. Kennepohl, R. T. Oakley, T. T.M. Palstra, Lynn Schneemeyer, S. R. Scott, J. V. Waszczak

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Abstract

The preparation and solid-state characterization of the bifunctional radicals [4,4′-(5-cyanobenzene)-l,3-bis(1,2,3,5-dithiadiazolyl)] and [4,4′-(5-cyanobenzene)-l,3-bis(1,2,3,5-diselenadiazolyl)] [5-CN-1,3-C6H3(CN2E2)2] (E = S, Se) are described. The crystals of the two title compounds are isomorphous and belong to the monoclinic space group P21/c, with (for E = S) a = 7.00(2), b = 30.050(6), c = 10.713(8) Å, β = 104.80(10)°, V = 2179(6) Å 3, Z = 8 and (for E = Se) a = 7.124(4), b = 30.50(2), c = 10.874(2) Å, β = 105.46(3)°, V = 2277(2) Å3, Z = 8. The crystal structures consist of stacks of diradicals running parallel to x; radical dimerization up and down the stack generates a zigzag arrangement, as seen in the related 1,3-phenylene structures. Along the stacking axis the mean intradimer E-E contacts are 3.12 (E = S) and 3.23 Å (E = Se), while the mean interdimer E---E distances are 3.89 (E = S) and 3.91 Å (E = Se). Magnetic and conductivity data are presented and discussed in light of extended Hückel band structure calculations.

Original languageEnglish
Pages (from-to)820-825
Number of pages6
JournalChemistry of Materials
Volume5
Issue number6
DOIs
StatePublished - 1 Jan 1993

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Dimerization
Benzene
Electronic properties
Band structure
Structural properties
Magnetic properties
Crystal structure
Crystals

Cite this

Cordes, A. W. ; Haddon, R. C. ; Hicks, R. G. ; Kennepohl, D. K. ; Oakley, R. T. ; Palstra, T. T.M. ; Schneemeyer, Lynn ; Scott, S. R. ; Waszczak, J. V. / Preparation and Solid-State Structural, Electronic, and Magnetic Properties of the 5-Cyano-1,3-benzene-Bridged Bis(1,2,3,5-dithiadiazolyl) and Bis(1,2,3,5-diselenadiazolyl) [5-CN-1,3-C6H3(CN2E2)2] (E = S, Se). In: Chemistry of Materials. 1993 ; Vol. 5, No. 6. pp. 820-825.
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title = "Preparation and Solid-State Structural, Electronic, and Magnetic Properties of the 5-Cyano-1,3-benzene-Bridged Bis(1,2,3,5-dithiadiazolyl) and Bis(1,2,3,5-diselenadiazolyl) [5-CN-1,3-C6H3(CN2E2)2] (E = S, Se)",
abstract = "The preparation and solid-state characterization of the bifunctional radicals [4,4′-(5-cyanobenzene)-l,3-bis(1,2,3,5-dithiadiazolyl)] and [4,4′-(5-cyanobenzene)-l,3-bis(1,2,3,5-diselenadiazolyl)] [5-CN-1,3-C6H3(CN2E2)2] (E = S, Se) are described. The crystals of the two title compounds are isomorphous and belong to the monoclinic space group P21/c, with (for E = S) a = 7.00(2), b = 30.050(6), c = 10.713(8) {\AA}, β = 104.80(10)°, V = 2179(6) {\AA} 3, Z = 8 and (for E = Se) a = 7.124(4), b = 30.50(2), c = 10.874(2) {\AA}, β = 105.46(3)°, V = 2277(2) {\AA}3, Z = 8. The crystal structures consist of stacks of diradicals running parallel to x; radical dimerization up and down the stack generates a zigzag arrangement, as seen in the related 1,3-phenylene structures. Along the stacking axis the mean intradimer E-E contacts are 3.12 (E = S) and 3.23 {\AA} (E = Se), while the mean interdimer E---E distances are 3.89 (E = S) and 3.91 {\AA} (E = Se). Magnetic and conductivity data are presented and discussed in light of extended H{\"u}ckel band structure calculations.",
author = "Cordes, {A. W.} and Haddon, {R. C.} and Hicks, {R. G.} and Kennepohl, {D. K.} and Oakley, {R. T.} and Palstra, {T. T.M.} and Lynn Schneemeyer and Scott, {S. R.} and Waszczak, {J. V.}",
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Preparation and Solid-State Structural, Electronic, and Magnetic Properties of the 5-Cyano-1,3-benzene-Bridged Bis(1,2,3,5-dithiadiazolyl) and Bis(1,2,3,5-diselenadiazolyl) [5-CN-1,3-C6H3(CN2E2)2] (E = S, Se). / Cordes, A. W.; Haddon, R. C.; Hicks, R. G.; Kennepohl, D. K.; Oakley, R. T.; Palstra, T. T.M.; Schneemeyer, Lynn; Scott, S. R.; Waszczak, J. V.

In: Chemistry of Materials, Vol. 5, No. 6, 01.01.1993, p. 820-825.

Research output: Contribution to journalArticleResearchpeer-review

TY - JOUR

T1 - Preparation and Solid-State Structural, Electronic, and Magnetic Properties of the 5-Cyano-1,3-benzene-Bridged Bis(1,2,3,5-dithiadiazolyl) and Bis(1,2,3,5-diselenadiazolyl) [5-CN-1,3-C6H3(CN2E2)2] (E = S, Se)

AU - Cordes, A. W.

AU - Haddon, R. C.

AU - Hicks, R. G.

AU - Kennepohl, D. K.

AU - Oakley, R. T.

AU - Palstra, T. T.M.

AU - Schneemeyer, Lynn

AU - Scott, S. R.

AU - Waszczak, J. V.

PY - 1993/1/1

Y1 - 1993/1/1

N2 - The preparation and solid-state characterization of the bifunctional radicals [4,4′-(5-cyanobenzene)-l,3-bis(1,2,3,5-dithiadiazolyl)] and [4,4′-(5-cyanobenzene)-l,3-bis(1,2,3,5-diselenadiazolyl)] [5-CN-1,3-C6H3(CN2E2)2] (E = S, Se) are described. The crystals of the two title compounds are isomorphous and belong to the monoclinic space group P21/c, with (for E = S) a = 7.00(2), b = 30.050(6), c = 10.713(8) Å, β = 104.80(10)°, V = 2179(6) Å 3, Z = 8 and (for E = Se) a = 7.124(4), b = 30.50(2), c = 10.874(2) Å, β = 105.46(3)°, V = 2277(2) Å3, Z = 8. The crystal structures consist of stacks of diradicals running parallel to x; radical dimerization up and down the stack generates a zigzag arrangement, as seen in the related 1,3-phenylene structures. Along the stacking axis the mean intradimer E-E contacts are 3.12 (E = S) and 3.23 Å (E = Se), while the mean interdimer E---E distances are 3.89 (E = S) and 3.91 Å (E = Se). Magnetic and conductivity data are presented and discussed in light of extended Hückel band structure calculations.

AB - The preparation and solid-state characterization of the bifunctional radicals [4,4′-(5-cyanobenzene)-l,3-bis(1,2,3,5-dithiadiazolyl)] and [4,4′-(5-cyanobenzene)-l,3-bis(1,2,3,5-diselenadiazolyl)] [5-CN-1,3-C6H3(CN2E2)2] (E = S, Se) are described. The crystals of the two title compounds are isomorphous and belong to the monoclinic space group P21/c, with (for E = S) a = 7.00(2), b = 30.050(6), c = 10.713(8) Å, β = 104.80(10)°, V = 2179(6) Å 3, Z = 8 and (for E = Se) a = 7.124(4), b = 30.50(2), c = 10.874(2) Å, β = 105.46(3)°, V = 2277(2) Å3, Z = 8. The crystal structures consist of stacks of diradicals running parallel to x; radical dimerization up and down the stack generates a zigzag arrangement, as seen in the related 1,3-phenylene structures. Along the stacking axis the mean intradimer E-E contacts are 3.12 (E = S) and 3.23 Å (E = Se), while the mean interdimer E---E distances are 3.89 (E = S) and 3.91 Å (E = Se). Magnetic and conductivity data are presented and discussed in light of extended Hückel band structure calculations.

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U2 - 10.1021/cm00030a017

DO - 10.1021/cm00030a017

M3 - Article

VL - 5

SP - 820

EP - 825

JO - Chemistry of Materials

JF - Chemistry of Materials

SN - 0897-4756

IS - 6

ER -