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Comparison of the structure property relationships in LB films of zwitterionic TCNQ adducts

Comparison of the structure property relationships in LB films of zwitterionic TCNQ adducts
Comparison of the structure property relationships in LB films of zwitterionic TCNQ adducts
Substitution reactions of TCNQ (7,7,8,8-tetracyanoquinodimethane) with suitable quinolinium and picolinium electron donor moieties yielded an extensive analogous series of alpha-bridged quinolinium and picolinium adducts R(2)Q3CNQ and R(2)P3CNQ respectively of which the long chain (Z)-{beta-[N-(1-hexadecyl)quinolinium-2-yl]-alpha-cyano-4-styryl}-dicyan omethanide (C16H33(2)Q3CNQ) is a typical example. These zwitterionic D-pi-A materials (where D and A are electron donor and acceptor respectively) exhibit properties such as solvatochromism, molecular rectification and second harmonic generation and were compared and contrasted to the existing gamma-bridged adducts. The behaviour of the materials on the water subphase and their resultant Langmuir-Blodgett (LB) film fabrication were studied. The abrupt change in molecular orientation in LB films of the gamma-bridged adducts occurring at R = C15H31 and above was not seen in the more flatly orientated alpha-bridged adducts. Further characterisation of the LB films was performed using reflectance-absorption infra-red spectroscopy (RAIRS) and surface plasmon resonance (SPR). The crystal structure of the long chain adduct, C10H21(2)Q3CNQ, is also reported.
langmuir-blodgett-films, rectifying characteristics, molecular rectifiers, crystal
1437-1445
Bell, Norman A.
6f601e84-74aa-4000-9017-b0e23dc747f0
Bradley, Christopher S.
df67638c-c070-4e38-8505-695e2474ae35
Broughton, Richard A.
393983c3-3094-4172-8d15-16331ccafa90
Coles, Simon J.
65bb28e4-4917-43f5-a770-a00017d6783f
Hibbs, David E.
92245583-6eb5-4afc-9093-57377cd6abf4
Hursthouse, Michael B.
a65b4d35-2ea0-47e7-938a-d744f4d9ba28
Ray, Asim K.
08137ced-6c32-46da-970b-8d69e1942875
Simmonds, Derek J.
8850790b-c3cf-487f-8711-426150e45d69
Thorpe, Stephen C.
902382e5-2b5e-421e-9e19-821fcc9d737c
Bell, Norman A.
6f601e84-74aa-4000-9017-b0e23dc747f0
Bradley, Christopher S.
df67638c-c070-4e38-8505-695e2474ae35
Broughton, Richard A.
393983c3-3094-4172-8d15-16331ccafa90
Coles, Simon J.
65bb28e4-4917-43f5-a770-a00017d6783f
Hibbs, David E.
92245583-6eb5-4afc-9093-57377cd6abf4
Hursthouse, Michael B.
a65b4d35-2ea0-47e7-938a-d744f4d9ba28
Ray, Asim K.
08137ced-6c32-46da-970b-8d69e1942875
Simmonds, Derek J.
8850790b-c3cf-487f-8711-426150e45d69
Thorpe, Stephen C.
902382e5-2b5e-421e-9e19-821fcc9d737c

Bell, Norman A., Bradley, Christopher S., Broughton, Richard A., Coles, Simon J., Hibbs, David E., Hursthouse, Michael B., Ray, Asim K., Simmonds, Derek J. and Thorpe, Stephen C. (2005) Comparison of the structure property relationships in LB films of zwitterionic TCNQ adducts. Journal of Materials Chemistry, 15 (14), 1437-1445. (doi:10.1039/b414325f).

Record type: Article

Abstract

Substitution reactions of TCNQ (7,7,8,8-tetracyanoquinodimethane) with suitable quinolinium and picolinium electron donor moieties yielded an extensive analogous series of alpha-bridged quinolinium and picolinium adducts R(2)Q3CNQ and R(2)P3CNQ respectively of which the long chain (Z)-{beta-[N-(1-hexadecyl)quinolinium-2-yl]-alpha-cyano-4-styryl}-dicyan omethanide (C16H33(2)Q3CNQ) is a typical example. These zwitterionic D-pi-A materials (where D and A are electron donor and acceptor respectively) exhibit properties such as solvatochromism, molecular rectification and second harmonic generation and were compared and contrasted to the existing gamma-bridged adducts. The behaviour of the materials on the water subphase and their resultant Langmuir-Blodgett (LB) film fabrication were studied. The abrupt change in molecular orientation in LB films of the gamma-bridged adducts occurring at R = C15H31 and above was not seen in the more flatly orientated alpha-bridged adducts. Further characterisation of the LB films was performed using reflectance-absorption infra-red spectroscopy (RAIRS) and surface plasmon resonance (SPR). The crystal structure of the long chain adduct, C10H21(2)Q3CNQ, is also reported.

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Published date: 2005
Keywords: langmuir-blodgett-films, rectifying characteristics, molecular rectifiers, crystal

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Local EPrints ID: 20720
URI: https://eprints.soton.ac.uk/id/eprint/20720
PURE UUID: e86394ca-02c9-4ed9-988d-6f400596ffa2

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Date deposited: 01 Mar 2006
Last modified: 17 Jul 2017 16:28

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Contributors

Author: Norman A. Bell
Author: Christopher S. Bradley
Author: Richard A. Broughton
Author: Simon J. Coles
Author: David E. Hibbs
Author: Michael B. Hursthouse
Author: Asim K. Ray
Author: Derek J. Simmonds
Author: Stephen C. Thorpe

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