Dipole Parallel-Aligned Organic Molecular Materials

DIPOLE PARALLEL-ALIGNED CRYSTALLINE ORGANIC MATERIALS

Polar Order

ALIGNED BIOMATERIALS
a-Helix
a-Helix Bundle
parallel coiled-coil a-helix (-)
antiparallel coiled-coil a-helix (-)
a,b-barrel ()

ALIGNED AMPHIPHILES - Gluconamides
OGA (1986, Saenger et al.)
HGA (1988, Saenger et al.)
DGA (1988, Saenger et al.)
UGA (1990, Jeffrey & Maluszynska)
HDGA (1995, Fuhrhop et al.)
GAC (2001, Masuda & Shimizu)

ALIGNED SALT MATERIALS
MC-PTS (1990, Okada et al.)
DAST (1994, Marder et al.)
M2DB2 (1996, Bosshard et al.)
DPP-HFP (2000, Coe et al.)

ALIGNED MOLECULAR MATERIALS
Para-Pyrrolidinyl Nitrobenzenes
NPP (1984, Zyss et al.)
PNP (1986, Wagniere et al.)

Biphenyls
nBCB (1987, Haase, et al.)
DMACB (1991, Zyss et al.)
AMB (2005, Knotts & Glaser)

Iodopyridines
PIP (1999, Ahrens & Jones)
DIIPY (2002, Pennington et al.)

Other Donor-Acceptor Materials
DAD (1991, Pu)
APDA (1996, Sagawa et al.)

Unit Cell
Dipole Lattice
Design

Azines with Double T-Contacts
MCA (2000, Lewis & Glaser)
MBA (1995, Chen & Glaser)
MIA (2001, Lewis & Glaser)

DFA (2003, Knotts & Glaser, unpublished)
DCA (2002, Knotts & Glaser, unpublished)
DBA (2002, Knotts & Glaser, unpublished)

Azines with Triple T-Contacts
PCA (2001, Lewis & Glaser, unpublished)
PBA (2001, Lewis & Glaser, unpublished)
PIA (2001, Lewis & Glaser, unpublished)

MBPFA (2004, Knotts & Glaser, unpublished)
MBPCA (2002, Knotts & Glaser, unpublished)
MBPBA (2002, Knotts & Glaser, unpublished)
MBPIA (2005, Knotts & Glaser, unpublished)

Click on the abbreviation of any material to jump to the entry for that material. Clicking in the area of any Lewis structure displays a molecular model of the experimentally determined crystal structure of that material. The CHIME plugin is required.

ALIGNED AMPHIPHILE MATERIALS

OGA = N-(n-octyl)-D-gluconamide

Zabel, V.; Müller-Fahrnow, A.; Hilgenfeld, R.; Saenger, W.; Pfannenmüller, B.; Enkelmann, V.; Welte, W. Chem. Phys. Lipids 1986, 39, 313-327.

C₁₄H₂₉NO₆ a = 5.252(1) Å b = 32.426(9) Å c = 4.805(1) Å
P2₁ a = 90° b = 94.96(5)° g = 90°

HGA = N-(n-heptyl)-D-gluconamide

Müller-Fahrnow, A.; Hilgenfeld, R.; Hesse, H.; Saenger, W.; Pfannenmüller, B. Carbohyr. Res. 1988, 176, 165.

C₁₃H₂₇NO₆ a = 5.183 Å b = 16.18 Å c = 4.803 Å
P1 a = 94.2° b = 96.1° g = 99.0°

DGA = N-(n-decyl)-D-gluconamide

Müller-Fahrnow, A.; Hilgenfeld, R.; Hesse, H.; Saenger, W.; Pfannenmüller, B. Carbohydr. Res. 1988, 176, 165.

C₁₆H₃₃NO₆ a = 5.255 Å b = 35.97 Å c = 4.807 Å
P2₁ a = 90° b = 94.81° g = 90°

UGA = N-(n-undecyl)-D-gluconamide

Jeffrey, G. A.; Maluszynska, H. Carbohydr. Res. 1990, 207, 211-219.

C₁₇H₃₅NO₆ a = 6.2267(6) Å b = 19.628(9) Å c = 4.7810(4) Å
P1 a = 93.23(2)° b = 95.60(1)° g = 89.58(2)°

HDGA = N-(n-hexadecyl)-D-gluconamide

Andre, C.; Luger, P.; Gutberlet, Y.; Vollhardt, D.; Fuhrhop, J.-H. Carbohydr. Res. 1995, 272, 129.

C₁₄H₂₉NO₆ a = 4.807 Å b = 46.771 Å c = 5.2885 Å
P2₁ a = 90° b = 90° g = 90.37°

GAC = 1-galactosamide carboxylic acid

Masuda, M.; Shimizu, F. Chem. Commun. 2001, 2442-2443.

C₂₂H₄₄NO₈ a = 4.90(1) Å b = 40.139(1) Å c = 6.289(1) Å
Monoclinic, P2₁ a = 90° b = 106.48(1)° g = 90°

ALIGNED SALT MATERIALS

MC-PTS = 1-Methyl-4-(2-(4-hydroxyphenyl)vinyl)pyridinium p-toluenesulfonate

Okada, S.; Masaki, A.; Matsuda, H.; Nakanishi, H.; Koike, T.; Ohmi, T.; Yoshikawa, N.; Umegaki, S. Jpn. J. Appl. Phys. 1990, 29, 1112.

C₁₄H₁₄NO⁺ C₇H₇O₃S^- a = 6.615 Å b = 7.971 Å c = 9.359 Å
Triclinic, P1 a = 105.63° b = 97.39° g = 95.40°

DAST = 4'-Dimethylamino-N-methyl-4-stilbazolium tosylate

Perry, J. W.; Marder, S. R.; Perry, K. J.; Sleva, E. T.; Yakymyshyn, C.; Stewart, K. R.; Boden, E. P. Chem. Mater. 1994, 6, 1137.

C₆H₁₉N₂⁺ C₇H₇SO₃^- a = 10.365 Å b = 11.322 Å c = 17.893 Å
Monoclinic, Cc a = 90.° b = 92.24° g = 90.°

M2DN2 = Merocyanine and 2,4-Dihydroxybenzaldehyde Monohydrate (actually contains that and 2,4,6-Trihydroxybenzaldehyde)

Pan, F.; Wong, M. S.; Gramlich, V.; Bosshard, C.; Guenter, P. J. Am. Chem. Soc. 1996, 118, 6315-6316. (Favorable alignment by way of dipole-antiparallel alignment of two chromophores: merocyanine and protonated merocyanine.)

C₁₅H₁₅NO₂, [C₁₅H₁₆NO₂]⁺, C₇H₆O₃, [C₇H₅O₄]^-, H₂O a = 8.262 Å b = 10.039 Å c = 13.491 Å
P1 a = 69.73° b = 82.99° g = 66.06°

DPP-HFP = trans-4-[4-(Dimethylamino)phenyliminomethyl]-N-phenylpyridinium hexafluorophosphate

Coe, B. J.; Harris, J. A.; Gelbrich, T.; Hursthouse, M. B. Acta Cryst. 2000, C56, 1487-1489.

C₂₀H₂₀N₃⁺ PF₆^- a = 19.3044 Å b = 10.6009 Å c = 12.6549 Å
Monoclinic, Cc a = 90.° b = 125.527° g = 90.°

ALIGNED MOLECULAR MATERIALS

Para-Pyrrolidinyl Nitrobenzenes

NPP = Name ...

Zyss, J.; Nicoud, J. F.; Coquillay, M. J. Chem. Phys. 1984, 81, 4160.

C₁₁H₁₄N₂O₃ a = 5.261 Å b = 14.908 Å c = 7.185 Å
Monoclinic, P2₁ a = 90.° b = 105.18° g = 90.°

PNP = Name ...

Dirk, C. W.; Twieg, R. J.; Wagniere, G J. Am. Chem. Soc. 1986, 108, 5387.

C₁₀H₁₃N₃O₃ a = 5.182 Å b = 14.964 Å c = 7.045 Å
Monoclinic, P2₁ a = 90.° b = 106.76° g = 90.°

Biphenyls

nBCB = 4'-n-Butoxy-4-cyanobiphenyl

Walz, L.; Paulus, H.; Haase, W. Z. Kristallogr. 1987, 180, 97.

C₁₇H₁₇NO a = 11.044 Å b = 9.087 Å c = 28.944 Å
Monoclinic, Pca21 a = 90.° b = 90.° g = 90.°

DMACB = Dimethylamino-4'-cyano-1,1'-biphenyl

Zyss, J.; Ledoux, I.; Bertault, M.; Toupet, E. Chem. Phys. 1991, 150, 125.

C₁₅H₁₄N₂ a = 9.503 Å b = 16.429 Å c = 8.954 Å
Triclinic, P1 a = 90.° b = 122.04° g = 90.°

AMB = 4-Acetyl-4'-methoxybiphenyl

Glaser, R.; Knotts, N.; Wu, Z.; and Barnes, C. L. Cryst. Growth Des. 2005, 5, xxx-xxx.

C₁₅H₁₄O₂ a = 7.900 Å b = 5.429 Å c = 26.80 Å
Orthorhombic, Pna2₁ a = 90.° b = 90.° g = 90.°

Iodopyridines

PIP = 4-Iodopyridine

Ahrens, B.; Jones, P. G. Acta Cryst. C 1999, 55, 1308.

C₅H₄IN a = 10.39 Å b = 14.394 Å c = 7.884 Å
Orthorhombic, Fdd2 a = 90° b = 90° g = 90°

DIIPY = 2,6-Diiodopyridine

Holmes, B. T.; Padgett, C. W.; Pennington, W. T. Acta Cryst. C 2002, 58, 147.

C₅H₃I₂N a = 6.8039 Å b = 17.011 Å c = 6.1959 Å
Orthorhombic, Fmm2 a = 90° b = 90° g = 90°

Others

DAD = (-)-1-(4-dimethylaminophenyl)-2-(2-hydroxypropylamino)cyclobutene-3,4-dione

PU, L. S. J. Chem. Soc., Chem. Commun. 1991, 429.

C₁₅H₁₈N₂O₃ a = 5.6932 Å b = 12.6790 Å c = 5.2500 Å
Triclinic, P1 a = 93.79° b = 103.77° g = 102.04°

APDA = 8-(4-Acetylphenyl)-1,4-dioxa-8-azaspiro(4.5)decane

Sagawa, M.; Kagawa, H.; Kakuta, A.; Kaji, M.; Saeki, M.; Namba, Y. Nonlinear Opt. 1996, 15, 147.

C₁₅H₁₉O₃N a = 6.875 Å b = 9.036 Å c = 21.676 Å
Orthorhombic, Pna2₁ a = 90° b = 90° g = 90°

Azines with Double T-Contacts

MCA = 4-Methoxy-4'-chloroacetophenone azine = 4-Methoxyacetophenone-(4'-chlorophenylethylidene) hydrazone.

Lewis, M.; Barnes, C. L.; Glaser, R. Acta Cryst. C 2000, 56, 393-396.

C₁₇H₁₇N₂OCl a = 6.3260 Å b = 31.465 Å c = 7.6680 Å
Triclinic, P1 a = 90.2640° b = 95.8910° g = 90.1540°

MBA = 4-Methoxy-4'-bromoacetophenone azine = 4-Methoxyacetophenone-(4'-bromophenylethylidene) hydrazone.

Chen, G. S.; Wilbur, J. K.; Barnes, C. L.; Glaser, R. J. Chem. Soc., Perkin Trans. 2 1995, 2311-2317.

C₁₇H₁₇N₂OBr a = 7.766 Å b = 31.949 Å c = 6.339 Å
Monoclinic, P21 a = 90.° b = 95.380° g = 90.°

MIA = 4-Methoxy-4'-iodoacetophenone azine = 4-Methoxyacetophenone-(4'-iodophenylethylidene) hydrazone.

Lewis, M.; Barnes, C.; Glaser, R. J. Chem. Crystallogr. 2001, 31, xxx-xxx.

C₁₇H₁₇N₂OI a = 6.4606 Å b = 7.2155 Å c = 33.5878 Å
Orthorhombic, Pna2₁ a = 90.° b = 90.° g = 90.°

DFA = 4-Decoxy-4'-fluoroacetophenone azine = 4-Decoxyacetophenone-(4'-fluorophenylethylidene) hydrazone.

Knotts, N.; Glaser, R., unpublished results.

C₂₆H₃₅N₂OF a = 6.4304 Å b = 7.5028 Å c = 24.411 Å
Triclinic, P1 a = 94.1420° b = 91.950° g = 96.219°

DCA = 4-Decoxy-4'-chloroacetophenone azine = 4-Decoxyacetophenone-(4'-chlorophenylethylidene) hydrazone.

Knotts, N.; Glaser, R., unpublished results.

C₂₆H₃₅N₂OCl a = 6.4668 Å b = 7.5009 Å c = 24.849 Å
Triclinic, P1 a = 93.210° b = 93.287° g = 96.033°

DBA = 4-Decoxy-4'-bromoacetophenone azine = 4-Decoxyacetophenone-(4'-bromophenylethylidene) hydrazone.

Knotts, N.; Glaser, R., unpublished results.

C₂₆H₃₅N₂OBr a = 6.4688 Å b = 7.5056 Å c = 25.099 Å
Triclinic, P1 a = 93.247° = 93.450° g = 95.956.°

Azines with Triple T-Contacts

PCA = 4-Phenoxy-4'-chloroacetophenone azine = 4-Phenoxyacetophenone-(4'-chlorophenylethylidene) hydrazone.

Lewis, M.; Glaser, R., unpublished results.

C₂₂H₁₉N₂OCl a = 19.8379 Å b = 7.2381 Å c = 6.4812 Å
Monoclinic, Pc a = 90.° b = 92.0160° g = 90.°

PBA = 4-Phenoxy-4'-bromoacetophenone azine = 4-Phenoxyacetophenone-(4'-bromophenylethylidene) hydrazone.

Lewis, M.; Glaser, R., unpublished results.

C₂₂H₁₉N₂OBr a = 19.995 Å b = 7.222 Å c = 6.482 Å
Monoclinic, Pc a = 90.° b = 91.585° g = 90.°

PIA = 4-Phenoxy-4'-iodoacetophenone azine = 4-Phenoxyacetophenone-(4'-iodophenylethylidene) hydrazone.

Lewis, M.; Glaser, R., unpublished results.

C₂₂H₁₉N₂OI a = 20.318 Å b = 7.2406 Å c = 6.4959 Å
Monoclinic, Pc a = 90.° b = 91.551° g = 90.°

MBPFA = 4-Fluoraacetophenone-(4'-methoxy-biphenyl-4"-yl)-ethylidene hydrazone

Knotts, N.; Glaser, R., unpublished results.

C₂₃H₂₁N₂OF a = 19.4309 Å b = 7.2170 Å c = 6.5163 Å
Monoclinic, Pc a = 90.° b = 98.795° g = 90.°

MBPCA = 4-Chloroacetophenone-(4'-methoxy-biphenyl-4"-yl)-ethylidene hydrazone

Knotts, N.; Glaser, R., unpublished results.

C₂₃H₂₁N₂OCl a = 6.2587 Å b = 39.240 Å c = 7.6710 Å
Monoclinic, P2₁ a = 90.° b = 95.941° g = 90.°

MBPBA = 4-Bromoacetophenone-(4'-methoxy-biphenyl-4"-yl)-ethylidene hydrazone

Knotts, N.; Glaser, R., unpublished results.

C₂₃H₂₁N₂OBr a = 6.3923 Å b = 7.2363 Å c = 40.927 Å
Orthorhombic, Pna2₁ a = 90.° b = 90.° g = 90.°

MBPIA = 4-Iodoacetophenone-(4'-methoxy-biphenyl-4"-yl)-ethylidene hydrazone

Knotts, N.; Glaser, R., unpublished results.

C₂₃H₂₁N₂OI a = 6.3980 Å b = 7.2597 Å c = 41.4797 Å
Orthorhombic, Pna2₁ a = 90.° b = 90.° g = 90.°

Polar Order ALIGNED BIOMATERIALS a-Helix a-Helix Bundle parallel coiled-coil a-helix (-) antiparallel coiled-coil a-helix (-) a,b-barrel ()
ALIGNED AMPHIPHILES - Gluconamides OGA (1986, Saenger et al.) HGA (1988, Saenger et al.) DGA (1988, Saenger et al.) UGA (1990, Jeffrey & Maluszynska) HDGA (1995, Fuhrhop et al.) GAC (2001, Masuda & Shimizu)
ALIGNED SALT MATERIALS MC-PTS (1990, Okada et al.) DAST (1994, Marder et al.) M2DB2 (1996, Bosshard et al.) DPP-HFP (2000, Coe et al.)
ALIGNED MOLECULAR MATERIALS Para-Pyrrolidinyl Nitrobenzenes NPP (1984, Zyss et al.) PNP (1986, Wagniere et al.) Biphenyls nBCB (1987, Haase, et al.) DMACB (1991, Zyss et al.) AMB (2005, Knotts & Glaser) Iodopyridines PIP (1999, Ahrens & Jones) DIIPY (2002, Pennington et al.) Other Donor-Acceptor Materials DAD (1991, Pu) APDA (1996, Sagawa et al.)	Unit Cell Dipole Lattice Design Azines with Double T-Contacts MCA (2000, Lewis & Glaser) MBA (1995, Chen & Glaser) MIA (2001, Lewis & Glaser) DFA (2003, Knotts & Glaser, unpublished) DCA (2002, Knotts & Glaser, unpublished) DBA (2002, Knotts & Glaser, unpublished) Azines with Triple T-Contacts PCA (2001, Lewis & Glaser, unpublished) PBA (2001, Lewis & Glaser, unpublished) PIA (2001, Lewis & Glaser, unpublished) MBPFA (2004, Knotts & Glaser, unpublished) MBPCA (2002, Knotts & Glaser, unpublished) MBPBA (2002, Knotts & Glaser, unpublished) MBPIA (2005, Knotts & Glaser, unpublished)

C₁₄H₂₉NO₆	a = 5.252(1) Å	b = 32.426(9) Å	c = 4.805(1) Å
P2₁	a = 90°	b = 94.96(5)°	g = 90°

C₁₃H₂₇NO₆	a = 5.183 Å	b = 16.18 Å	c = 4.803 Å
P1	a = 94.2°	b = 96.1°	g = 99.0°

C₁₆H₃₃NO₆	a = 5.255 Å	b = 35.97 Å	c = 4.807 Å
P2₁	a = 90°	b = 94.81°	g = 90°

C₁₇H₃₅NO₆	a = 6.2267(6) Å	b = 19.628(9) Å	c = 4.7810(4) Å
P1	a = 93.23(2)°	b = 95.60(1)°	g = 89.58(2)°

C₁₄H₂₉NO₆	a = 4.807 Å	b = 46.771 Å	c = 5.2885 Å
P2₁	a = 90°	b = 90°	g = 90.37°

C₂₂H₄₄NO₈	a = 4.90(1) Å	b = 40.139(1) Å	c = 6.289(1) Å
Monoclinic, P2₁	a = 90°	b = 106.48(1)°	g = 90°

C₁₄H₁₄NO⁺ C₇H₇O₃S^-	a = 6.615 Å	b = 7.971 Å	c = 9.359 Å
Triclinic, P1	a = 105.63°	b = 97.39°	g = 95.40°

C₆H₁₉N₂⁺ C₇H₇SO₃^-	a = 10.365 Å	b = 11.322 Å	c = 17.893 Å
Monoclinic, Cc	a = 90.°	b = 92.24°	g = 90.°

C₁₅H₁₅NO₂, [C₁₅H₁₆NO₂]⁺, C₇H₆O₃, [C₇H₅O₄]^-, H₂O	a = 8.262 Å	b = 10.039 Å	c = 13.491 Å
P1	a = 69.73°	b = 82.99°	g = 66.06°

C₂₀H₂₀N₃⁺ PF₆^-	a = 19.3044 Å	b = 10.6009 Å	c = 12.6549 Å
Monoclinic, Cc	a = 90.°	b = 125.527°	g = 90.°

C₁₁H₁₄N₂O₃	a = 5.261 Å	b = 14.908 Å	c = 7.185 Å
Monoclinic, P2₁	a = 90.°	b = 105.18°	g = 90.°

C₁₀H₁₃N₃O₃	a = 5.182 Å	b = 14.964 Å	c = 7.045 Å
Monoclinic, P2₁	a = 90.°	b = 106.76°	g = 90.°

C₁₇H₁₇NO	a = 11.044 Å	b = 9.087 Å	c = 28.944 Å
Monoclinic, Pca21	a = 90.°	b = 90.°	g = 90.°

C₁₅H₁₄N₂	a = 9.503 Å	b = 16.429 Å	c = 8.954 Å
Triclinic, P1	a = 90.°	b = 122.04°	g = 90.°

C₁₅H₁₄O₂	a = 7.900 Å	b = 5.429 Å	c = 26.80 Å
Orthorhombic, Pna2₁	a = 90.°	b = 90.°	g = 90.°

C₅H₄IN	a = 10.39 Å	b = 14.394 Å	c = 7.884 Å
Orthorhombic, Fdd2	a = 90°	b = 90°	g = 90°

C₅H₃I₂N	a = 6.8039 Å	b = 17.011 Å	c = 6.1959 Å
Orthorhombic, Fmm2	a = 90°	b = 90°	g = 90°

C₁₅H₁₈N₂O₃	a = 5.6932 Å	b = 12.6790 Å	c = 5.2500 Å
Triclinic, P1	a = 93.79°	b = 103.77°	g = 102.04°

C₁₅H₁₉O₃N	a = 6.875 Å	b = 9.036 Å	c = 21.676 Å
Orthorhombic, Pna2₁	a = 90°	b = 90°	g = 90°

C₁₇H₁₇N₂OCl	a = 6.3260 Å	b = 31.465 Å	c = 7.6680 Å
Triclinic, P1	a = 90.2640°	b = 95.8910°	g = 90.1540°

C₁₇H₁₇N₂OBr	a = 7.766 Å	b = 31.949 Å	c = 6.339 Å
Monoclinic, P21	a = 90.°	b = 95.380°	g = 90.°

C₁₇H₁₇N₂OI	a = 6.4606 Å	b = 7.2155 Å	c = 33.5878 Å
Orthorhombic, Pna2₁	a = 90.°	b = 90.°	g = 90.°

C₂₆H₃₅N₂OF	a = 6.4304 Å	b = 7.5028 Å	c = 24.411 Å
Triclinic, P1	a = 94.1420°	b = 91.950°	g = 96.219°

C₂₆H₃₅N₂OCl	a = 6.4668 Å	b = 7.5009 Å	c = 24.849 Å
Triclinic, P1	a = 93.210°	b = 93.287°	g = 96.033°

C₂₆H₃₅N₂OBr	a = 6.4688 Å	b = 7.5056 Å	c = 25.099 Å
Triclinic, P1	a = 93.247°	= 93.450°	g = 95.956.°

C₂₂H₁₉N₂OCl	a = 19.8379 Å	b = 7.2381 Å	c = 6.4812 Å
Monoclinic, Pc	a = 90.°	b = 92.0160°	g = 90.°

C₂₂H₁₉N₂OBr	a = 19.995 Å	b = 7.222 Å	c = 6.482 Å
Monoclinic, Pc	a = 90.°	b = 91.585°	g = 90.°

C₂₂H₁₉N₂OI	a = 20.318 Å	b = 7.2406 Å	c = 6.4959 Å
Monoclinic, Pc	a = 90.°	b = 91.551°	g = 90.°

C₂₃H₂₁N₂OF	a = 19.4309 Å	b = 7.2170 Å	c = 6.5163 Å
Monoclinic, Pc	a = 90.°	b = 98.795°	g = 90.°

C₂₃H₂₁N₂OCl	a = 6.2587 Å	b = 39.240 Å	c = 7.6710 Å
Monoclinic, P2₁	a = 90.°	b = 95.941°	g = 90.°