Fluorine-Based Crystal Engineering - ACS Symposium Series (ACS

Chapter 29

Fluorine-Based Crystal Engineering

Downloaded by UNIV OF OTTAWA on March 18, 2013 | http://pubs.acs.org Publication Date: July 21, 2005 | doi: 10.1021/bk-2005-0911.ch029

Taizo Ono and Yoshio Hayakawa Research Institute of Instrumentation Frontier, National Institute of Advanced Industrial and Science Technology (AIST), 2266-98, Anagahora, Shimoshidami, Moriyama, Nagoya 463-8560, Japan

Hybrid compounds R -X-R consisting of perfluoro and hydro moieties, R and R , which are connected with X functionality, are described. New crystal engineering based on these hybrid compounds is proposed as a rational method for the design of the functional materials. Hexafluoropropene trimers are selected as the fluoro synthons. A systematic investigation on the crystal structures of the hybrid compounds revealed that there are five packing motifs in connection with the topology of the molecules. Topochemical requirements for the solid -state polymerization of diacetylene functionality were satisfied with the precise tuning by tailor-made hybrid synthons. As a result, a black crystalline material with a metallic luster was synthesized. This new fluorine-based crystal engineering will be one of the unique molecular design methods for the material science. F

F

498

H

H

© 2005 American Chemical Society

In Fluorine-Containing Synthons; Soloshonok, V.; ACS Symposium Series; American Chemical Society: Washington, DC, 2005.


499 Highly ordered supramolecular structures are ubiquitous in nature from organic to inorganic realms. The most sophisticated structures seen in living organisms are the results of the cooperation of the intermolecular forces, after a bottom-up process based on the covalent architecture of the molecules. A crystal is also a highly ordered supramolecular bottom-up expression of molecules with enticing beauty and thus has attracted many scientists. In accordance with the surge of nanotechnology, the strong desire for the rational design of the highly ordered materials rekindled and gave an impetus to the research in crystal engineering as one of the most important tools in the supramolecular science (7). However, our understanding of the way of assemblage of molecules is yet in the embryonic stage (2). Thus, the apriori prediction of the crystal structures seems to be an awful challenge or impossible (3). According to Desiraju, a general solution to this problem would bring in a billion dollars to the pharmaceutical industry and a possible Nobel Prize to whoever cracks it (4). In this context, engineering the crystal packing, instead of the ab initio prediction of the crystal packing of any given molecules, could be a more realistic approach for the design of crystalline materials. A variety of molecular interactions have been investigated for aligning the molecules by using so-called supramolecular synthons approach (5). Most of the attention has been paid to the hydrogen-bonding-based synthons due mainly to an impetus from the DNA base pair structures (6). A stronger ionic bond has been widely used to make the structures (7). Recent advancement in the metalligand coordination is also striking (8). In contrast to these strong bonds, we will focus on the weak non-bonded interactions in this chapter. First, we introduce various types of inter-molecular synthons, which have been used in crystal engineering. Second, we survey the fluorine-based crystal engineering, and then explain our recently devised crystal engineering based on the fluorine-containing hybrid compounds, R -X-R . F

H

Crystal Engineering based on the weak non-bonded intermolecular interactions Also molecules for which no strong molecular interaction is expected crystallize in many cases. X-ray analysis of such crystals has revealed the existence of a variety of weak non-bonded interactions. Charge-transfer interactions (9), weak hydrogen bonds, and halogen-halogen interactions are seen in the following combination of intermolecular synthons. Charge-transfer interactions: π-π interactions (10), C-X (X=F, Cl, Br, I) — π systems (//), halogen bondings between a halogen and a lone pair of


500


electrons of hetero atoms (N, O, S etc.); π-π interaction and halogen bonding recently immerged as new tools for the crystal engineering in an interdisciplinary connection with fluorine chemistry. Weak hydrogen bondings: C-H—X (X=0, N , Cl, F, and an aromatic π system); Weak hydrogen bondings are recent concerns in this field (12). Halogen-halogen interactions: C-X—X-C (X=C1, Br, I); The halogenhalogen interaction has been taken as a subject of crystal engineering due to a ubiquitous appearance of such interactions in the organic halides (73).

Fluorine-based crystal engineering There has been reported some crystal engineering based on the fluoro organic compounds. One strategy is based on the fluorine's size, Η-mimicry, to finely tune the crystal packing of the organic molecules with a subtle change of the molecular shape by partial substitutions of H(s) of the molecules with F(s) (14). Some other reports claim C-H—F-C hydrogen bonding synthons or π—FC synthons for the crystal engineering (15) but the existence itself for such kinds of weak interactions are still controversial (16). Another fluorine-based crystal engineering, which has been recently reported by a Resnati group, is very innovative. Their method is based on another fluorine's unique property, its extremely high electronegativity. The method opened the door in an interdisciplinary field between supramolecular and fluorine chemistries (17). The group showed the high potentiality of the approach by an elegant application for a chiral resolution of halofluorocarbons which is otherwise impossible (18). The unique system he devised is the halogen bonding strengthened in the perfluorocarbon-halogen synthons (19). Halogen bonding itself has been known for a long time (20), but its elegant use in the crystal engineering has been realized by his new idea to use the R - X — N , Ο (X=Br, I) bases interactions for aligning the molecules. This type of fluorostrengthened halogen bonding is stronger than the hydrogen bonding (21). The details are to be referred to the next relevant chapter. Another way of the fluorine's use in the molecular assemblage is based on a face-to-face stacking between perfluoro aromatics and non-fluorinated aromatics (22). However, the C-F—H-C interactions prevail over the above-mentioned π-π stackings in some cases (23). This strategy is now actively investigated for a specific material design (24). Recently proposed fluoro specific interactions of anions with perfluoro aromatic compounds (25) and fluoroaromaticfluoroaromatic interactions are needed to be investigated further (26). F


501


Crystal engineering by the fluorine-containing hybrid compounds In contrast to the former fluorine-based crystal engineering methods, our fluorine-containing hybrid compound method is based on a different uniqueness of fluorine's property, i.e. its extremely low polarizability. This property gives the perfluoro compounds a repelling nature against both oil and water. This nature of the perfluoro group gives to the fluoro organic compounds a unique molecular recognizing capability when forming a supramolecular architecture (27). Conventional crystal engineering has focused on the attractive forces, but we focused on such a repelling nature (very weak dispersive interaction in genuine meaning) offluorineto the non-fluorine elements. This lipophobic and hydrophobic fluorine's nature, called sometimes as "fluorophilic", has been a hot topic in the recentfluorouschemistry (28). The fluorous chemistry is a liquid technology characterized by the fluorous phase separation. Our crystal technology is based on the corresponding phenomenon seen in the solid state. Fluoro segregation, or fluoro bilayer structure in the crystalline phase is very ubiquitous in the X-ray structures of the organo fluorine compounds having a perfluoro subtitutent (29). This micro phase segregation is the result of the "very stern molecular recognition" caused by the very uniquefluorine'sfluorophilic nature. With this simple packing phenomenon in mind, we initiated a systematic structural investigation on thefluorine-containinghybrid synthons having the structure of R -X-R (R and R are perfluorinated and non-fluorinated groups and X is a junction group) to find the packing-structure relationship in the belief that such systematic investigation of the structure-packing relationship will give us a bottom-up process towards crystalline materials. F

H

F

H

(a) (b) (c) Scheme 1 (a) Perfluorinated blocks (filled boxes) and hydrocarbon blocks (open boxes) each form its own phase in a liquid state, (b) Hybrids of per fluorinated and hydrocarbon blocks form a homogeneous phase, (c) On crystallization, hybrids self-assemble to a fluoro- and hydro-segregated supramolecular architecture.


502

One of the most important points we would like to emphasize here is that the formation of the fluorous segregated supramolecular assemblage, the features commonly seen in the crystal packing, was realized by the molecular hybridization of fluoro- and hydro-blocks. This fluorous segregation is in sharp contrast with the simple separation of perfluorinated and non-fluorinated blocks if not hybridized (see the cartoon in scheme 1). It should be reminded that the work on the nickel dithiolene complex with CF substitutents reported by Fournigue et al. is also based on control of the crystal packing by the fluorine's extremely low polarizability (30). Downloaded by UNIV OF OTTAWA on March 18, 2013 | http://pubs.acs.org Publication Date: July 21, 2005 | doi: 10.1021/bk-2005-0911.ch029

2

Requirement for the fluorinated synthons, R - X - R F

H

The characters required for the fluorinated hybrid synthons are summarized as follows. 1. Hybrid compounds should be crystalline. 2. Enough size of fluoro segment for molecular recognition by fluorophilicity and fluorophobicity for the supramolecular alignment. 3. Easy preparation in high-yield and with a flexible design. 4. Fluoro segment should be commercially available, not expensive, desirably produced in an industrial scale. Commercially available perfluoro olefins could be a choice for the purpose. Hexafluoropropene dimers are conceivable, but some attempts showed the difficulty in the crystallization and the size as the fluoro blocks seems to be not enough large for the solid state fluorous technology as is analogously seen in the liquid phase fluorous technology, i.e., miscible nature of perfluorohexane and hexane. We chose hexafluoropropene trimers as the fluoro synthons, as it satisfies all the above requirements.

Synthesis of the fluorinated synthons, R - X - R F

H

We fixed the R moiety and took the R moiety as a variable to get an insight into the crystal packing and structure relationship. An ether linkage was used for X due to the synthetic convenience and easiness of crystallization and the function's stability (31). The imine linkage might be also a choice for X, but it proved to be not suitable due mainly to the non-crystalline nature and due partly to the instability of the function and the poor yields (32). The variables RH used are summarized with the yield data in Table 1. F

H


503

Table 1. Structures of the hybrid compounds, R -0-R F

1(97.5%)

2(94.8%)

3(41.2%)

ζ Λ Downloaded by UNIV OF OTTAWA on March 18, 2013 | http://pubs.acs.org Publication Date: July 21, 2005 | doi: 10.1021/bk-2005-0911.ch029

7(98.3%)

ο

/γγ 15(quantit.)

5(99.2%)

12 (97.7%)

Q 16(quantit.)

6(97.8%)

^cf

Λ

8(quantit.)

11 (quantit.)

4(90%)

H

9(99.8%)

Ô „

10(quantit.)

( 9 g

„ .^P° (96

g%)

Y

FsC

CF3

CF AF 3

3

The reaction was conducted in DMF at room temperature with a slight excess of a hexafluoropropene trimer mixture consisting of F-4-methyl-3isopropyl-2-pentene (T-2) and F-2-methyl-3-isopropyl-2-pentene (T-3) and the phenol derivatives (T-3 reacts as T-2 due to a fast equilibrium between T-2 and T-3 under the conditions used). The products are purified by using fluorous phase technique (extraction with FC-72) or by subjecting to a simple short-path silica gel column. Nearly quantitative yields were attained by these simple procedures in all cases. High quality crystals with a few millimeter sizes are obtained in almost all cases so that the potential application could be conceivable for the design of the non-linear optical materials.

Crystal structures of the fluoro synthons All crystals are X-ray grade crystals and analyzed by the direct methods available in the teXan program package. All compounds have same common features of the packing, thus the hybrid molecules are aligned to form the segregated fluoro- and hydro-segments in the crystal packing. No exception appeared so that this micro phase separation is very robust. Therefore, the fluorine's effect of hexafluoropropene trimer was proved to be strong enough for the micro-fluorous phase formation. It is maybe that the shape of the globular R and non-globular R synergistically contribute to this micro-phase separation (33). One of the representative crystal packings is shown in Fig. 1. F

H



504

Fig. 1 A crystal packing of the hybrid molecule 12: biphenyl moiety disordered in two conformations with 1 : 1 occupancy, one of which and hydrogen atoms are omit for clarity. The hybrid molecules aligned in the anti-parallel manner with a biphenyl moiety overlapped. The formation of alternating fluoro- and hydro-layers is quite clear with segregated layer structures in the packing diagram. A main driving force should be the attraction between the hydrocarbon moieties of the hybrid molecules and at the same time thefluorine'srepelling nature against the hydrocarbon, fluorophobic from the viewpoint of the hydrocarbon side, fluorophilicfromthe viewpoint of the fluorine's side. Recently, Row emphasized the F-F interactions found in the organic fluorine compounds (34), Such F-F interactions are claimed analogously to the known Cl-Cl interactions, but still quite obscure and remained to be discussed in the future. In accordance with the Row's view and contrary to our understanding on the driving force of the micro fluorous formation, it is noteworthy to point the disorder structure found in the crystal packing of this compound. The scaffold for the packing of this hybrid compound seems to be the fluoro moiety of the hybrid molecule judging from the circumstantial evidence of the disorder structure seen only in the biphenyl moiety but not in the fluoro moiety (one of the disorder structures was omitted for the sake of clarity). Disorder structures are frequently seen in the fluoro moiety in thefluoro-substitutedmolecules due to their weak interactions with the surrounding contacted molecules. The fluoro moieties lined together to form a fluorous segregated layer and the wholefluorosegment was buried in this micro fluorous phase. Taking into account the weak F-F interactions in addition to the stronger C-H—aromatic interactions, it is very intriguing to find the disorder structure only in the two aromatic rings but not in the fluoro part. This kind of reversed disorder structure seen here is the first reported case to the best of our


505 knowledge. We analyzed all packings throughout the compounds and deduced the found packing modes into five packing motifs (Scheme 2).


Ο

perfluoroalkyl group

Qj

hydrocarbon group

Scheme 2 Five packing motifs found in the hybrid molecules

The quantitative analysis of structure-packing relationship remained to be done, but even qualitative structure-packing relationship is useful to expect the packing of the designed molecules by the topological analogy. The application for the material science of our new method shown in the next paragraph will testify the potential.

Application for the design of electron-conducting polymer To show the usefulness of this fluorine-based crystal engineering we chose motif 2 as an example for the molecular design of conjugated polymers, which are interesting materials with semiconducting and unique optical properties, applicable for LED and sensing devises (35). The structure and ORTEP figure of the fluoro synthon (10), which belongs to the motif 2, is shown in Fig. 2. The stereo view of the crystal packing of 10 is shown in Fig. 3.

Fig. 2 The structural formula and ORTEPfigureof the hybrid compound 10



506

Fig, 3. A stereo view of the crystal packing of 10 which belongs to motif 2

We designed the molecules, DA-(n,m), having a diacetylene function in the middle of the long alkyl chain of 10. The structure and ORTEP figure of the compound DA-(9,12) are shown in Fig. 4. As is expected from the molecular structure, the long alkyl chain bends at the both ends of the diacetylene moiety. This structural disturbance, however, did not change the packing mode (Fig. 5) so that the type 2 packing was proven to be rather robust and reserved intact all through. If the type 2 packing holds in the whole series of diacetylene derivatives, we can do the fine tuning of the mutual distance and orientation of diacetylene functions in the crystal packing by changing the carbon numbers m and η in the series, thus the topological requirement for the solid state polymerization could be realized in a certain combination of m and n. We therefore planned the synthesis of the compounds having several combinations of m and n.

Fig. 4 The structural formula and ORTEP figure of the hybrid compound DA(9,12)



Fig. 5 A crystal packing of the hybrid compound DA-(9,12)

Synthesis of designed fluoro synthons with diacetylene group The synthesis of the fluoro synthons DA-(n,m) having diacetylene functionality is outlined in scheme 3. First, lithiated terminal alkynes was brominated, then coupled with co-hydroxyl terminal alkynes under the presence of cuprous chloride to give the desired w-alkanol with a diacetylene function in the middle of the long alkyl chain in 32-51% isolated yields. The obtained alcohols were condensed with benzoic acid having a fluoro moiety by using DCC to give the desired fluoro synthons in fairly good yields (82-95%). The benzoic acid with a fluoro moiety was easily prepared by the reaction of phydroxybenzoic acid with one of the isomer of hexafluoropropene trimers, F2,4-dimethyl-3-ethyl-2-pentene, in high yield.


508 (i) HC==CC H m

8rC=CC H

2 m + 1

m

2 m

+i

(ii) HO(CH ) C=C—C=CC H 2

n

m

2 m + 1

(iii) R

(i)

f

° ~ \ _ /

_

(

C

H

l)w-BuLi/hexane, 2) B r

H O N H HCl/aq. E t N H 2


2 ) n

=

C

(ii)

2

~ ~

C

=

C

C

m

H

2 m

HC=C(CH ) OH 2

n

+

1

, CuCl,

32-51% yields in the processes (i) and (ii)

2

(iii) R 0 - ^ ^ ~ C 0 H F

C

2

, D C C , 4 - D M P 82-95% yields

Scheme 3

Solid-state uv-initiated polymerization of fluoro synthons The solid-state uv-initiated polymerization of DA-(n,m) was carried out by irradiating the crystals dispersed in perfluorodecalin under Ar atmosphere at ambient temperatures (36). The low-pressure 6W Hg lamp was used as the uv source. The photopolymerizability was summarized in Table 2.

Table 2 Photopolymerizability of the hybrid diacetylene derivatives Diacetylene Derivatives

Photopolymerizability

DA-(3,3)

-

DA-(3,4)

-

DA-(4,3)

-

DA-(4,4)

+

DA-(9,8)

-

DA-(9,9)

+

DA-(9,10)

+

DA-(9,U)

-

DA-(9,12)

-


509


The clear transparent crystals of DA-(9,9), and DA-(9,10) were colored to the blue soon after the irradiation and its color deepened within a minute and then to the black within next few minutes. The crystals of DA-(4,4) is also polymerizable but less reactive. These uv-initiated photopolymerizations occur only in a solid state but not at all in a liquid state even under the presence of radical initiator of AIBN at elevated temperatures. The surface of the blackcolored crystals had a metal luster as is shown in Fig. 6.

Fig. 6 The black-colored crystals of compound DA-(9,9) with a metallic luster which were obtained by the solid-state uv-initiated photopolymerization.

The crystal packing of the uv-stable DA-(9,12) showed the diacetylene moieties lined in an anti-parallel manner with the closest distance of 0.686 nm. As is expectedfromthe distance, the crystals of DA-(9,12) remained unchanged after a prolonged time of uv-irradiation. On the other hand, the crystal packing of the uv-sensitive DA-(9,9), which was X-ray analyzed at lower temperature (120°C), revealed the corresponding distance between the diacetylene moieties is as close as 0.379 nm. The crystals of DA-(9,10) are too sensitive to X-ray irradiation and thus, we were not able to analyze the compound even at lower temperatures. Therefore, the distances between the diacetylene functions should be shorter. In contrast to our solid state photopolymerization, thermally initiated topochemical polymerization of diacetylene derivatives which were designed based on a logical host-guest approach has recently been reported (37). The


510

rational design of the topochemical solid-state reaction is still very difficult, however, the fluorine-based crystal engineering including our hybrid fluoro synthon method will be continually exploited and revised in more sophisticated manners for the more reliable molecular design (38).

Summary The crystalline compounds having the hybrid structures withfluorinatedR and unfluorinated R parts connected by a junction group X , R -X-R , are systematically investigated by X-ray diffraction method. The packing modes found in a series of hybrid compounds are featured by the micro phase separation with segregated fluoro layers, which are grouped into 5 packing motifs. The new fluorine-based crystal engineering was devised based on the topological relationships between the packing motifs and the molecular structures. The usefulness of this methodology was proven by the molecular design for the photopolymerization. The crystals of the designed diacetylene derivatives successfully polymerized under uv irradiation to give black-colored crystalline materials with a metal luster. We believe that our new crystal engineering is still in its infancy stage but its potential is high and will be used in many ways, especially in the field of the functional material design. F


H

F

H

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28.


29.

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31. 32. 33. 34.

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