4,4′-[(2,7-Dibromo­fluorene-9,9-di­yl)dimethyl­ene]dipyridinium bis­(perchlorate)

Xuan, Z.; Zhao, S.; Lu, L.; Wang, X.; Yang, X.

doi:10.1107/S1600536810021859

organic compounds

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ISSN: 2056-9890

Volume 66| Part 7| July 2010| Page o1718

doi:10.1107/S1600536810021859

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4,4′-[(2,7-Dibromofluorene-9,9-diyl)dimethylene]dipyridinium bis(perchlorate)

Zongwei Xuan,^a ^* Shanshan Zhao,^b Lude Lu,^a Xin Wang ^a and Xujie Yang ^a

^aMaterials Chemistry Laboratory, Nanjing University of Science and Technology, Nanjing 210094, People's Republic of China, and ^bNew Materials & Function Coordination Chemistry Laboratory, Qingdao University of Science and Technology, Qingdao Shandong 266042, People's Republic of China
^*Correspondence e-mail: zhaopusu@163.com, xzwqd@163.com

(Received 13 May 2010; accepted 8 June 2010; online 18 June 2010)

In the crystal of the title compound, C₂₅H₂₀Br₂N₂²⁺·2ClO₄⁻, intermolecular N—H⋯O and C—H⋯O hydrogen bonds, along with C—H⋯π interactions, stabilize the crystal structure.

Related literature

A variety of ligands of different molecular dimensions and functional properties have been utilized in the preparation of numerous supramolecular assemblies with exotic architectures, see: Applegarth et al., (2005 ). For related structures, see: Meerssche et al. (1979 , 1980 ).

Experimental

Crystal data

C₂₅H₂₀Br₂N₂²⁺·2ClO₄⁻
M_r = 707.15
Monoclinic, C 2/c
a = 15.605 (3) Å
b = 11.267 (2) Å
c = 16.318 (3) Å
β = 117.60 (3)°
V = 2542.6 (11) Å³
Z = 4
Mo Kα radiation
μ = 3.45 mm⁻¹
T = 295 K
0.25 × 0.20 × 0.18 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (North et al., 1968 ) T_min = 0.441, T_max = 0.537
11835 measured reflections
2915 independent reflections
2611 reflections with I > 2σ(I)
R_int = 0.062
3 standard reflections every 100 reflections intensity decay: none

Refinement

R[F² > 2σ(F²)] = 0.039
wR(F²) = 0.103
S = 1.06
2915 reflections
177 parameters
H-atom parameters constrained
Δρ_max = 1.01 e Å⁻³
Δρ_min = −0.79 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg3 is the centroid of the C1–C6 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O3	0.86	2.24	2.997 (3)	148
C11—H11A⋯O1	0.93	2.57	3.196 (3)	125
C12—H12A⋯O4ⁱ	0.93	2.44	3.193 (3)	138
C13—H13A⋯O1ⁱⁱ	0.93	2.47	3.376 (3)	164
C10—H10A⋯Cg3	0.93	2.93	3.688 (2)	140
Symmetry codes: (i) $[-x+1, y, -z+{\script{1\over 2}}]$ ; (ii) $[x, -y+1, z+{\script{1\over 2}}]$ .

Data collection: CAD-4 Software (Enraf–Nonius, 1989 ); cell refinement: CAD-4 Software; data reduction: NRCVAX (Gabe et al., 1989 ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL/PC (Sheldrick, 2008); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810021859/hg2685sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810021859/hg2685Isup2.hkl

checkCIF report

Comment top

A variety of ligands of different molecular dimensions and functional properties were utilized for the preparation of numerous supramolecular assemblies of exotic architectures as reported in the recent literature (Applegarth et al., 2005). Herein, we report a new bipyridine derivative of 2,7-dibromo-9,9-(4-pyridyl-methyl) fluorene [DBPMF].

scheme I

The structure of the title compound contains a protonated 2,7-dibromo-9,9-bis(4-pyridinium-methyl) fluorene dications DBPMFH₂²⁺ and two perchlorate anions ClO₄^-. All the bond lengths and bond angles in the phenyl ring and five-membered ring are corresponding with those observed in 2-acetylaminofluorene (Meerssche et al., 1980) and 4-acetylamino-fluorene (Meerssche et al., 1979). Two bromine atoms along with the thirteen atoms of fluorenyl ring are coplanar (P1) and the biggest deviation is 0.038Å for C6 atom. The dihedral angle between the plane P1 and the pyridyl ring containing N1 atom is 72.11 (2)°.

In the crystal lattice, there are four types of supramolecular interactions (Table 1), including N—H···O hydrogen bonds, C—H···O potential hydrogen bonds, C—H···π supramolecular interaction and π–π stacking interactions. Among these supramolecular interactions, the two types N—H···O hydrogen bonds link two DBPMFH₂²⁺ cations with two ClO₄^- anions to construct one-dimensional chains, then the other supramolecular interactions help the 1D chains to form three-dimensional net-works, which stabilize the crystal structure.

Related literature top

A variety of ligands of different molecular dimensions and functional properties have been utilized in the preparation of numerous supramolecular assemblies with exotic architectures, see: Applegarth et al., (2005). For related structures, see: Meerssche et al. (1979, 1980).

Experimental top

DBPMF was synthesized by the reaction of 2,7-dibromofluorene (3.24 g, 0.01 mol) and 4-chloromethyl pyridine hydrochloride (1.64 g, 0.02 mol) in DMSO (70 ml). The title compound was obtained by the reaction of DBPMF (2.55 g, 5.0 mmol) and HClO₄ (0.26 ml, 5.0 mmol) in EtOH (50 ml). Single crystals suitable for x-ray measurements were obtained by recrystallization at room temperature.

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software (Enraf–Nonius, 1989); data reduction: NRCVAX (Gabe et al., 1989); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL/PC (Sheldrick, 2008); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

Fig. 1. The structure of the title compound showing 30% probability displacement ellipsoids and the atom-numbering scheme.

4,4'-[(2,7-Dibromofluorene-9,9-diyl)dimethylene]dipyridinium bis(perchlorate) top

Crystal data top

C₂₅H₂₀Br₂N₂²⁺·2ClO₄⁻	F(000) = 1408
M_r = 707.15	D_x = 1.847 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 25 reflections
a = 15.605 (3) Å	θ = 4–14°
b = 11.267 (2) Å	µ = 3.45 mm⁻¹
c = 16.318 (3) Å	T = 295 K
β = 117.60 (3)°	Block, yellow
V = 2542.6 (11) Å³	0.25 × 0.20 × 0.18 mm
Z = 4

Data collection top

Enraf–Nonius CAD-4 diffractometer	2611 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.062
Graphite monochromator	θ_max = 27.5°, θ_min = 3.1°
ω/2θ scans	h = −20→20
Absorption correction: ψ scan (North et al., 1968)	k = −14→14
T_min = 0.441, T_max = 0.537	l = −21→21
11835 measured reflections	3 standard reflections every 100 reflections
2915 independent reflections	intensity decay: none

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.103	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0681P)² + 0.5103P] where P = (F_o² + 2F_c²)/3
2915 reflections	(Δ/σ)_max = 0.001
177 parameters	Δρ_max = 1.01 e Å⁻³
0 restraints	Δρ_min = −0.79 e Å⁻³

Crystal data top

C₂₅H₂₀Br₂N₂²⁺·2ClO₄⁻	V = 2542.6 (11) Å³
M_r = 707.15	Z = 4
Monoclinic, C2/c	Mo Kα radiation
a = 15.605 (3) Å	µ = 3.45 mm⁻¹
b = 11.267 (2) Å	T = 295 K
c = 16.318 (3) Å	0.25 × 0.20 × 0.18 mm
β = 117.60 (3)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	2611 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.062
T_min = 0.441, T_max = 0.537	3 standard reflections every 100 reflections
11835 measured reflections	intensity decay: none
2915 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	0 restraints
wR(F²) = 0.103	H-atom parameters constrained
S = 1.06	Δρ_max = 1.01 e Å⁻³
2915 reflections	Δρ_min = −0.79 e Å⁻³
177 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Br1	−0.201221 (15)	0.319251 (18)	−0.114789 (15)	0.01844 (12)
N1	0.33006 (13)	0.39368 (16)	0.24329 (14)	0.0178 (4)
H1A	0.3819	0.3707	0.2418	0.021*
C1	−0.13197 (15)	0.2901 (2)	0.01439 (16)	0.0153 (4)
C2	−0.11455 (16)	0.17300 (17)	0.04368 (17)	0.0162 (5)
H2A	−0.1377	0.1115	0.0009	0.019*
C3	−0.06207 (15)	0.14838 (19)	0.13788 (15)	0.0154 (4)
H3A	−0.0500	0.0704	0.1589	0.019*
C4	−0.02836 (14)	0.24228 (18)	0.19940 (15)	0.0140 (4)
C5	−0.04692 (14)	0.36049 (18)	0.16834 (16)	0.0141 (4)
C6	−0.09989 (14)	0.38606 (18)	0.07490 (15)	0.0146 (4)
H6A	−0.1134	0.4638	0.0536	0.017*
C7	0.0000	0.4457 (2)	0.2500	0.0123 (5)
C8	0.07543 (14)	0.52981 (17)	0.24235 (15)	0.0136 (4)
H8A	0.0429	0.5737	0.1849	0.016*
H8B	0.0965	0.5870	0.2924	0.016*
C9	0.16421 (14)	0.47237 (18)	0.24518 (15)	0.0133 (4)
C10	0.16000 (15)	0.39694 (18)	0.17545 (15)	0.0157 (4)
H10A	0.1004	0.3722	0.1290	0.019*
C11	0.24415 (15)	0.35912 (19)	0.17540 (16)	0.0175 (4)
H11A	0.2413	0.3098	0.1285	0.021*
C12	0.33797 (15)	0.46320 (19)	0.31370 (16)	0.0183 (4)
H12A	0.3986	0.4841	0.3605	0.022*
C13	0.25553 (15)	0.50303 (18)	0.31584 (15)	0.0152 (4)
H13A	0.2606	0.5505	0.3645	0.018*
Cl1	0.41022 (4)	0.31707 (4)	0.05644 (4)	0.01488 (15)
O1	0.31184 (11)	0.35890 (17)	0.01812 (12)	0.0258 (4)
O2	0.41264 (16)	0.19359 (15)	0.03767 (15)	0.0321 (5)
O3	0.45717 (12)	0.33505 (14)	0.15648 (12)	0.0213 (4)
O4	0.46088 (12)	0.38494 (16)	0.01772 (12)	0.0286 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.02330 (17)	0.01761 (16)	0.01334 (17)	−0.00066 (7)	0.00760 (12)	−0.00009 (7)
N1	0.0150 (8)	0.0174 (9)	0.0236 (10)	0.0018 (7)	0.0112 (8)	0.0021 (8)
C1	0.0146 (9)	0.0182 (9)	0.0130 (10)	−0.0009 (8)	0.0064 (8)	0.0001 (9)
C2	0.0211 (11)	0.0122 (10)	0.0171 (12)	−0.0033 (7)	0.0105 (10)	−0.0052 (8)
C3	0.0200 (10)	0.0111 (9)	0.0167 (11)	0.0006 (8)	0.0097 (9)	0.0000 (9)
C4	0.0152 (9)	0.0124 (9)	0.0165 (11)	0.0002 (7)	0.0090 (8)	0.0018 (8)
C5	0.0144 (9)	0.0106 (9)	0.0196 (11)	−0.0009 (7)	0.0097 (8)	−0.0020 (9)
C6	0.0158 (9)	0.0119 (9)	0.0171 (10)	−0.0002 (7)	0.0086 (8)	0.0008 (8)
C7	0.0125 (12)	0.0115 (13)	0.0135 (14)	0.000	0.0064 (11)	0.000
C8	0.0160 (9)	0.0095 (8)	0.0167 (10)	−0.0007 (7)	0.0088 (8)	0.0001 (8)
C9	0.0162 (9)	0.0108 (9)	0.0152 (10)	−0.0005 (7)	0.0091 (8)	0.0032 (8)
C10	0.0165 (9)	0.0158 (10)	0.0154 (10)	−0.0007 (8)	0.0079 (8)	0.0000 (8)
C11	0.0207 (10)	0.0148 (10)	0.0201 (12)	0.0005 (8)	0.0121 (9)	0.0000 (9)
C12	0.0153 (9)	0.0183 (10)	0.0184 (11)	−0.0014 (8)	0.0054 (8)	0.0019 (9)
C13	0.0181 (10)	0.0134 (9)	0.0135 (10)	−0.0010 (8)	0.0068 (8)	0.0017 (8)
Cl1	0.0145 (3)	0.0161 (3)	0.0132 (3)	−0.00181 (16)	0.0057 (2)	−0.00099 (17)
O1	0.0162 (8)	0.0345 (9)	0.0247 (9)	0.0037 (7)	0.0077 (7)	0.0074 (8)
O2	0.0390 (10)	0.0178 (9)	0.0283 (11)	−0.0006 (7)	0.0061 (9)	−0.0061 (7)
O3	0.0210 (8)	0.0273 (8)	0.0128 (8)	−0.0003 (6)	0.0055 (7)	−0.0034 (7)
O4	0.0253 (8)	0.0390 (10)	0.0264 (9)	−0.0070 (7)	0.0161 (7)	0.0037 (8)

Geometric parameters (Å, º) top

Br1—C1	1.900 (2)	C7—C8	1.561 (2)
N1—C11	1.342 (3)	C8—C9	1.510 (3)
N1—C12	1.348 (3)	C8—H8A	0.9700
N1—H1A	0.8600	C8—H8B	0.9700
C1—C2	1.387 (3)	C9—C10	1.397 (3)
C1—C6	1.392 (3)	C9—C13	1.399 (3)
C2—C3	1.394 (3)	C10—C11	1.381 (3)
C2—H2A	0.9300	C10—H10A	0.9300
C3—C4	1.384 (3)	C11—H11A	0.9300
C3—H3A	0.9300	C12—C13	1.378 (3)
C4—C5	1.407 (3)	C12—H12A	0.9300
C4—C4ⁱ	1.468 (4)	C13—H13A	0.9300
C5—C6	1.387 (3)	Cl1—O2	1.4289 (18)
C5—C7	1.526 (3)	Cl1—O4	1.4395 (17)
C6—H6A	0.9300	Cl1—O1	1.4423 (16)
C7—C5ⁱ	1.526 (3)	Cl1—O3	1.4609 (19)
C7—C8ⁱ	1.561 (2)

C11—N1—C12	122.30 (19)	C9—C8—C7	116.89 (17)
C11—N1—H1A	118.9	C9—C8—H8A	108.1
C12—N1—H1A	118.9	C7—C8—H8A	108.1
C2—C1—C6	123.1 (2)	C9—C8—H8B	108.1
C2—C1—Br1	117.84 (18)	C7—C8—H8B	108.1
C6—C1—Br1	119.06 (17)	H8A—C8—H8B	107.3
C1—C2—C3	119.4 (2)	C10—C9—C13	117.85 (19)
C1—C2—H2A	120.3	C10—C9—C8	122.64 (18)
C3—C2—H2A	120.3	C13—C9—C8	119.28 (19)
C4—C3—C2	118.7 (2)	C11—C10—C9	120.1 (2)
C4—C3—H3A	120.7	C11—C10—H10A	119.9
C2—C3—H3A	120.7	C9—C10—H10A	119.9
C3—C4—C5	121.1 (2)	N1—C11—C10	119.8 (2)
C3—C4—C4ⁱ	130.12 (13)	N1—C11—H11A	120.1
C5—C4—C4ⁱ	108.75 (13)	C10—C11—H11A	120.1
C6—C5—C4	120.7 (2)	N1—C12—C13	119.5 (2)
C6—C5—C7	129.05 (19)	N1—C12—H12A	120.2
C4—C5—C7	110.21 (19)	C13—C12—H12A	120.2
C5—C6—C1	117.00 (19)	C12—C13—C9	120.3 (2)
C5—C6—H6A	121.5	C12—C13—H13A	119.8
C1—C6—H6A	121.5	C9—C13—H13A	119.8
C5—C7—C5ⁱ	102.1 (2)	O2—Cl1—O4	110.40 (13)
C5—C7—C8ⁱ	112.17 (11)	O2—Cl1—O1	110.72 (12)
C5ⁱ—C7—C8ⁱ	112.75 (11)	O4—Cl1—O1	109.07 (11)
C5—C7—C8	112.75 (11)	O2—Cl1—O3	108.98 (11)
C5ⁱ—C7—C8	112.17 (11)	O4—Cl1—O3	108.89 (10)
C8ⁱ—C7—C8	105.2 (2)	O1—Cl1—O3	108.74 (11)

Symmetry code: (i) −x, y, −z+1/2.

Hydrogen-bond geometry (Å, º) top

Cg3 is the centroid of the C1–C6 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O3	0.86	2.24	2.997 (3)	148
C11—H11A···O1	0.93	2.57	3.196 (3)	125
C12—H12A···O4ⁱⁱ	0.93	2.44	3.193 (3)	138
C13—H13A···O1ⁱⁱⁱ	0.93	2.47	3.376 (3)	164
C10—H10A···Cg3	0.93	2.93	3.688 (2)	140

Symmetry codes: (ii) −x+1, y, −z+1/2; (iii) x, −y+1, z+1/2.

Experimental details

Crystal data
Chemical formula	C₂₅H₂₀Br₂N₂²⁺·2ClO₄⁻
M_r	707.15
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	295
a, b, c (Å)	15.605 (3), 11.267 (2), 16.318 (3)
β (°)	117.60 (3)
V (Å³)	2542.6 (11)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	3.45
Crystal size (mm)	0.25 × 0.20 × 0.18

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.441, 0.537
No. of measured, independent and observed [I > 2σ(I)] reflections	11835, 2915, 2611
R_int	0.062
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.103, 1.06
No. of reflections	2915
No. of parameters	177
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.01, −0.79

Computer programs: CAD-4 Software (Enraf–Nonius, 1989), NRCVAX (Gabe et al., 1989), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL/PC (Sheldrick, 2008), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

Cg3 is the centroid of the C1–C6 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O3	0.8600	2.2356	2.997 (3)	147.53
C11—H11A···O1	0.9300	2.5687	3.196 (3)	125.18
C12—H12A···O4ⁱ	0.9300	2.4428	3.193 (3)	137.77
C13—H13A···O1ⁱⁱ	0.9300	2.4712	3.376 (3)	164.43
C10—H10A···Cg3	0.9300	2.9260	3.688 (2)	140.07

Symmetry codes: (i) −x+1, y, −z+1/2; (ii) x, −y+1, z+1/2.

Acknowledgements

The authors would like to thank the Natural Science Foundation of Shandong Province (No. Y2007B14).

References

Applegarth, L., Goetra, A. E. & Steed, J. W. (2005). Chem. Commun. 18, 2405–2406. Web of Science CSD CrossRef Google Scholar
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Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
Gabe, E. J., Le Page, Y., Charland, J.-P., Lee, F. L. & White, P. S. (1989). J. Appl. Cryst. 22, 384–387. CrossRef CAS Web of Science IUCr Journals Google Scholar
Meerssche, M., Germain, G., Declercq, J. P. & Touillaux, R. (1979). Cryst. Struct. Commun. 8, 119–122. Google Scholar
Meerssche, M., Germain, G., Declercq, J. P., Touillaux, R., Roberfroid, M. & Razzouk, C. (1980). Cryst. Struct. Commun. 9, 515–518. Google Scholar
North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351–359. CrossRef IUCr Journals Web of Science Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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4,4′-[(2,7-Di­bromo­fluorene-9,9-di­yl)di­methyl­ene]dipyridinium bis­­(perchlorate)

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

4,4′-[(2,7-Dibromofluorene-9,9-diyl)dimethylene]dipyridinium bis(perchlorate)