TY - JOUR
T1 - Structural Trends in Potential Organic Conductors Based on (Donor–CH2)2 Tetracyanoquinodimethane Molecules
AU - Becker, J. Y.
AU - Bernstein, J.
AU - Bittner, S.
AU - Sarma, J. A.R.P.
AU - Shaik, S. S.
PY - 1989/7/1
Y1 - 1989/7/1
N2 - The stoichiometry of electron donor-acceptor (EDA) complexes with potential electrical conductivity may be predetermined by preparing compounds in which D(s) and A(s) are chemically linked. The structural properties of three compounds comprised of two identical Ds bonded to one A (TCNQ; i.e., D…A…D) are reported here. The three compounds are isostructural; monoclinic, space group P21/a, Z = 2. D = C6H5: a = 13.999 (6), b = 10.760 (2), c = 6.970 (2) Å, β = 102.51 (3)°. D = p–C6H4OCH3: a = 16.887 (6), b = 10.235 (6), c = 7.172 (4) Å, β = 107.80 (4)°. D = β-naphthyl: a = 16.93 (4), b = 11.676 (8), c = 7.093 (9) Å, β = 114.3 (1)°. The structure of the last compound has also been determined at 93 K: a = 16.816 (5), b = 11.438 (4),c = 7.086 (1) Å,β = 115.21 (3)°. The outstanding common structural feature is the tendency to form infinite segregated stacks of A along the c axis, thus achieving a condition necessary for electrical conductivity. The charge-transfer interaction is achieved by the formation of previously not observed D…A…D triplets along both the A stacks and linking screw-related stacks. Details of the interactions leading to this unusual architecture are investigated with the aid of lattice energy calculations.
AB - The stoichiometry of electron donor-acceptor (EDA) complexes with potential electrical conductivity may be predetermined by preparing compounds in which D(s) and A(s) are chemically linked. The structural properties of three compounds comprised of two identical Ds bonded to one A (TCNQ; i.e., D…A…D) are reported here. The three compounds are isostructural; monoclinic, space group P21/a, Z = 2. D = C6H5: a = 13.999 (6), b = 10.760 (2), c = 6.970 (2) Å, β = 102.51 (3)°. D = p–C6H4OCH3: a = 16.887 (6), b = 10.235 (6), c = 7.172 (4) Å, β = 107.80 (4)°. D = β-naphthyl: a = 16.93 (4), b = 11.676 (8), c = 7.093 (9) Å, β = 114.3 (1)°. The structure of the last compound has also been determined at 93 K: a = 16.816 (5), b = 11.438 (4),c = 7.086 (1) Å,β = 115.21 (3)°. The outstanding common structural feature is the tendency to form infinite segregated stacks of A along the c axis, thus achieving a condition necessary for electrical conductivity. The charge-transfer interaction is achieved by the formation of previously not observed D…A…D triplets along both the A stacks and linking screw-related stacks. Details of the interactions leading to this unusual architecture are investigated with the aid of lattice energy calculations.
UR - http://www.scopus.com/inward/record.url?scp=0012288663&partnerID=8YFLogxK
U2 - 10.1021/cm00004a007
DO - 10.1021/cm00004a007
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AN - SCOPUS:0012288663
SN - 0897-4756
VL - 1
SP - 412
EP - 420
JO - Chemistry of Materials
JF - Chemistry of Materials
IS - 4
ER -