Preparation and liquid crystalline behaviour of a series of semifluorinated allylic monomers

Article abstract of DOI:10.1080/15421400590955127

A series of smectic liquid-crystalline 4,4'-biphenyl derivatives incorporating a perfluorinated segment and an allylic part have been prepared and their mesomorphic properties investigated. The preparation of these compounds has been done from 2-F-butylethyl iodide, the 2-F-hexylethyl iodide or the 2-F-octylpropanoic acid. The physical properties of these novel fluorinated materials are commented and illustrated in comparison with four homologous allylic series previously described. The choice of the molecular design of these monomers allows us to obtain dimorphism and high mesomorphic range determined from differential thermal analysis and the light microscopy.

Full text of DOI:10.1080/15421400590955127

Mol. Cryst. Liq. Cryst., Vo l. 43 6, pp. 23 7 =[ 119 1] –24 6 =[ 120 0] , 2 00 5
Co py ri g h t # T ay l o r & Fr an ci s In c.
I SSN : 1 54 2- 14 0 6 pri n t =15 63- 528 7 on l i ne
DOI : 1 0. 1 08 0/ 1 54 2 14 0 0 59 095 5127
Preparation and Liquid Crystalline Behaviour of a Series
of Semifluorinated Allylic Monomers
E li s ab e th T af f i n de Gi ve n c hy
Fr e´ d e´ ri c G ui ttar d
Lau r e n t C ai l l i e r
J ua n M un ue r a
S e rge Ge ri bal d i
L ab ora t oire de C h imi e de s M a t e´ ria u x O rg a n iq ue s e t M e´ t a lliq u e s
(
C . M. O. M . ) , F a cu lt e´ de s S cie nc es , U n iv ers i t e´ de N ice S o ph ia - A nt ipo lis ,
P arc V alro s e, N ice C e dex , F ra n ce
0
A series of smectic liquid-crystalline 4,4 -biphenyl derivatives incorporating a
perfluorinated segment and an allylic part have been prepared and their meso-
morphic properties investigated. The preparation of these compounds has been
done from 2-F-butylethyl iodide, the 2-F-hexylethyl iodide or the 2-F-octylpropa-
noic acid. The physical properties of these novel fluorinated materials are commen-
ted and illustrated in comparison with four homologous allylic series previously
described. The choice of the molecular design of these monomers allows us to
obtain dimorphism and high mesomorphic range determined from differential
thermal analysis and the light microscopy.
Key w or ds: dim or phi sm; f lu or i na t e d ; mo l ec u la r d es ign ; s me c tic
1. INTRODUCTION
The int r o d uc t io n of f luo ri n a t ed p a rt s , w hi ch a re not com p a t i bl e, i n
a p o ly me r , c an p ro d u ce a se g reg a t io n i nt o d i st i n ct mi cr od om a i ns
t h at is fa v o ur ab l e t o t he a p p ea r a nce of a w el l org a n i ze d p ha se such
a s m ai nly s me c t i c l iq ui d cr ys ta l p ha se s [ 1– 4 ]. F urt h erm ore, one of
t h e m o st im p o r t a nt p a ra me t er f or t he us e a s L .C . d ev i ces i s t he
w i d e t e m p e r at u re ra ng e of me so mo rp h i sm , w i t h ena n t i ot rop y a nd
Th e a ut h ors t ha n k A t of in a f or t h e gi ft o f p er fl u or o alky la te d r aw ma te r ia ls . L C
t h a nks M ENRT for a gr a n t .
Add res s c orr es pond en c e t o Fr e´ d e´ r ic G ui t t a r d, La b o r at oi r e d e Ch im ie d e s M at e´ r ia ux
O r ga n iq ues et M e´ t a ll i qu e s ( C.M .O.M .), Fa c u lt e´ d es Sc i e nc e s, Un iv e rs it e´ d e Nic e S op h ia -
An t ipolis , Pa r c Va lr os e, 0 6 1 0 8 Ni ce C ed ex 2 , Fr a n ce . E - mai l: g ui tt ar d @ un ic e .f r
23 7=[ 11 91 ]

2
38=[1 1 9 2 ]
E. T. de Givenchy et al.
re p r o d uc ibi li t y, d uri ng t he p ha se t ra nsi t i on p hen ome na , b ut a l so t he
che m ic al an d t he rm a l st a b il i t y . Pe r f luo ri n a t ed t a i l s a re a l so chem i-
cal ly s ta bl e , p o s ses s v er y l ow v is cos i t y a nd ca n i ncrea s e t he st a b i li t y
o f t he r e sul t ing me so p h a ses . It i s w or t h no t i ng t ha t t he na t ure of
t h e s pa c er , bo u nd ing t he p er f l uori na t ed ta i l s t o t he ri g i d cor e ca n
g o ve r n an d fu rt he rm or e ‘‘e xa ce rb a t e’ ’ t he p ro- sm ect o g eni c ef fect of
F-a lk yl at e d c hai n s [ 5– 1 1 ] . Thi s k i nd of a rr an g eme nt ca n b e used fo r
sur fa c e t re a t m en t t o re a ch f or ex a m p l e l ow surf a ce en erg y ma t eri a l s
[
(
12 –1 4 ]. So , t he p re p a ra t i on of f luo ri na t ed l i qui d cry st a l p ol y mer s
L CPs ) is o f a gr ea t -i nt er es t cl a ss of ma t e r i a ls b eca use t hey com bi ne
t h e an i s o tr o p y of l iq u i d cr ys t a ll i ne me so p has es , t he i n t ri nsi c rem ar k-
a bl e p ro p e r ti e s of t h e p ol y me r b ac k b o ne ( mec ha ni ca l p rop ert i es a nd
g la ss y s ta t e as a n ex a m p l e) a nd t he p ec uli a r p rop ert i es of fl uor in a t ed
p a r t. In o r de r t o p re p ar e t hi s k i nd of st r uct ure , i t i s i mp ort a n t t o w el l
d es ign t he m o n om er s w hi ch ex hi b it LC p ro p ert i es . I n t h i s st ud y w e
p re se n t o m e ga uns at ur at ed mo nom er s a s raw ma t er i a ls fo r ho mop o l y -
me r iz a ti o n o r fo r g r a ft i ng p ol y h y d rog e nos i lo x a ne b a ckb o ne. I n ord e r t o
f ind o u t t he be s t mo le c ul ar a rra ng em ent p a ra me t ers i nsi d e t he mon o-
me r , w e ha ve t ak e n i nt o a cco un t p re vi ou s com p a ri son of fl uor i na t ed
v iny lic m o no m er s d es c ri b ed i n t he l it e ra t ure [1 5 , 1 6 ] . I n fa ct , t he sy s-
t em a t ic va ri a t io n of mo le c ul ar st r uct ur e co mb i ne d w i t h d et er mi na t i on
o f k e y p hy si co -c he mi ca l p ro p er t ie s i s a co rner st one fo r est a b l i s hi ng
st r u c tu re p ro p e r t y re la t i on shi p i n me so mor p hi c fi el d .
T he ai m o f t hi s w or k i s t o d es ig n a nd d esc ri b e t he sy nt hes i s of new
b ip he ny l c o mp o u nd s ( se e Fi g . 1 ) p re c urs or s of hi g hl y fl uor i na t ed p ol y -
me r s. T he se c o m p ou nd s w i ll p re s en t a b ip heny l mes og e ni c cor e, l i nked
t o a va ri o u s -le ng t h f luo ri na t ed t a il t hro u g h a n est e r l i nker . T he L .C .
p h as e s o f t he s e co mp ou n d s w er e cha ra ct eri z ed b y a com bi n a t i on of
F IG URE 1 I nv e s t ig at ed a lly lic m on o m ers .

LC Behaviour of Fluorinated Allylic Monomers
23 9=[ 11 93 ]
d if f e r en t ial s cann ing ca l ori m et r y ( D .S.C . ) a nd op t i c a l p ol a ri z ed
m i cr o s co p y (P . O .M . ) me t hod s.
2
2
. EXPERIMENTAL PART
.1. Materials
Al l t h e c he m ic a ls w er e p urc ha s ed f rom A ld ri ch a nd Acr os Che m i ca l
Co . an d w e re use d w i t ho ut a ny f urt he r p uri fi ca t i on . Unl ess sp eci f ie d
a s d ry , t he s o lve nt s w er e unp ur if i ed re a g e nt g ra d e. T he p roc ed ure
f o r t he p re p ar at i on of 2 - F- al k y l p ro p an oi c a ci d s a re d escr ib e d el se-
w he r e [1 7] . P e rfl uo r i nat e d ra w ma t e r i al s we r e g i v en b y At of i na .
2.2. Methods
Co nf ir m at io n o f t he st r uct ur es w a s ob t a i ned b y Nucl ea r Ma g net i c
Re s o na nc e (N. M . R .) a nd M a ss Sp ec t ro m et ry (M .S. ). N. M. R. sp ec-
t ro s c o py w as c arr ie d ou t usi ng a B ruk er A C 2 0 0 MH z sp ec t rom et er .
S pe c t ra w e r e r e co r d ed usi ng d eu te ra t ed so lv ent w i t h T MS a s i nt erna l
1
1 9
re fe r e nc e fo r H N.M .R . a nd C FC l f or F N. M . R. . M. S. w a s ca rri e d
3
o u t us ing a T he r mo Fi nni ga n sp e ct ro m et e r a nd a n EI mod e a t 7 0 eV .
Th e p u r it y o f t he mo nom er s w a s d et e rm ine d b y t hi n l a y er chro m a t o-
g r ap h y. T he ini t ia l p ha se a ssi g n me nt s a nd cor resp o nd i ng t ra nsi t i on
t e m p e r at ur e s w er e d et e rm ine d usi ng a n O l ym p us BX 6 0 op t i ca l mi cro -
sco p e e qu ip p e d w i th cr os se d p ol a ri ze r s. The sa mp l es w er e t herm o-
st a t e d by m e an s of a Li nk a m Sci en t i f i c I nst rum ent s L TS 3 5 0
he at in g uni t an d TM S 9 4 t em p er a tu re co ntr o l b y t he sa me ma nuf ac -
t u r e r. T e m p e ra t ur es a nd en t hal p i e s of t ra nsi t i on w er e i n v est i g a t ed
b y D . S. C. us ing a Pe rk i n E lm er D SC 7 i nst r ume nt . Sa mp l e s of
5
– 10 m g w e r e pl a ce d i n a l um ini um ca p sul e s a nd he a t ed i n a st a t i c
ni t ro g e n at m o s p he re. The he at i ng a nd co oli ng curv es w er e ob t a i ned
ꢀ
ꢁ1
a t t h e r a t e o f 10 C mi n . The p ha se t ra nsi t i on t emp era t ure s of t he
m o n o m e rs w e re ex t ra p o l a t ed a s t he on set t emp era t ure s.
2.3. Synthesis
The s ynt he s is of 4 -[ 4 - ( Al l yl o x yp h en y l) ] p hen y l -3 -( p erf l uoro - n-a l k yl )-
p ro p an o at e (E C 4 , E C 6 a nd E C 8 ) w a s ca rri e d ou t i n t w o st ep s a s
sh o w e d in F igu r e 2 . Y ie ld s f or a ll co mp ou nds a re rep o r t ed i n T a bl e 1 .
4-(4-Allyloxyphenyl)phenol (2)
In a 10 0 m L r o und b ot t o m f la sk eq ui p p ed w i t h a cond e ns er, 2 0 mmo l
o f s o di um hy dr o xi d e w a s d i lut e d i n 9 mL o f w a t e r. T hen 1 0 mmo l of

2
40=[1 1 9 4 ]
E. T. de Givenchy et al.
F IG URE 2 Sy n t h e ti c pa t h wa y t o m on o m ers . R e a g en t s a n d co n dit io n s : ( i) M g ,
E t O, C O , ( ii) B r C H , N aO H , H O=E t O H re f lu x t h e n H C l, ( iii) D C C ,
C H = C H
D MA P, 12 h , rt .
2
2
2
2
2
4
-( 4-h yd r o xyp h en yl ) p heno l w a s a d d ed sl ow l y a nd a l lo w ed t o rea ct a t
ro o m t e m p e r at ure . A ft e r 2 0 mi nu t es , 1 0 mo l o f a l ly l b rom id e w a s a d d ed
d ro p w is e an d t h e so lut i on w a s st i rre d und e r ref l ux fo r 8 hour s. Af t er
co o lin g d o w n, th e so lut i o n w a s f il t ra t ed t o rem ov e t he rem ai ni ng
0
4
,4 -b ip he no la te . The re sul t i ng w hi t e so li d w a s p oure d i nt o a 1 0 %
H C l aq ue o u s s o lut i o n, st i rre d f or 2 0 mi nu t es a nd t he sol ut i on w a s fi l -
t ra t e d ag ai n. T he 4 -( 4 - A ll y lo xy p hen y l) p he no l so i sol a t ed (T he p uri f i -
ca t io n o f t he 4- ( 4- A ll y lo xy p he nyl ) p he nol i nt e rm ed i a t e i s b a sed fro m
t he d iff e re n c e o f so lub i l i t y b et w ee n t he mon o a nd t he d i sub s t i t ut ed
co mp o un ds ) w as re cry s t a ll iz ed f rom et h anol . Y i el d 4 5 %.
T ABL E 1 Y ield s f o r A lly lic M o no m e rs
Cpd s
R
F
va l ue
Yi el d %
O ve r a ll %
1
1
2
EC 4
EC 6
EC 8
a
b
4
6
–
4
6
8
5 4
4 0
4 0
7 5
8 1
9 0
–
–
–
3 0
3 3
3 6

LC Behaviour of Fluorinated Allylic Monomers
24 1=[ 11 95 ]
1
H NM R (C DC l =TM S, d p p m , J Hz ), 4 , 62 (2 H , O CH CH CH , d ,
3
2
2
J ¼ 5, 3 ), 5, 3 5 (1H , O CH C HCH , d d , J ¼ 1 0 ,5 J ¼ 1 , 5) , 5 , 48 (1 H ,
2
2
O C H CH CH , d d , J ¼ 1 7, 3 J ¼ 1 ,5 ) , 6 ,0 8 (1 H , O CH CHCH , m ,
2
2
2
2
J ¼ 10 , 5 J ¼ 17 , 3 J ¼ 5 ,3 ) , 7 ,0 0 t o 7 ,5 ( 8H ) .
a r
4-[4-(Allyloxyphenyl)]phenyl-3-(perfluoro-n-alkyl)propanoate
(EC4, EC6 and EC8)
Es t e ri fic at io n of 2 w i t h 2 - F- al k y lp r op a no i c a ci d s p rev i ous l y p re-
p a r e d (2 - F-b u t yl p rop a no ic a ci d a nd 2 - F- hexy l p ro p a n oi c a ci d ) or com -
m e rc ia lly av ai lab l e ( 2- F- oct y lp r op a no i c a c i d ) w a s p erf orme d usi n g
d ic y c lo he xy l c ar bo d i i mi d e ( D CC ) ca t a ly z ed by 4 -( N,N-d i m et hy l a mi no) -
p y r id ine . In a t y p ica l ex p e rim en t , a sus p ensi o n of 1 1 mmo l of 2 - F-
a l ky lp r o p an o ic a ci d s a nd 1 0 mm ol of 4 -( 4 -a l l yl ox y p heny l )p he no l ( 2 )
in 30 m L d ry d ic hl or om et ha ne w a s p re p ar ed . T hen 1 1 mmo l of d i cy cl o-
he xy lc ar b o d iim id e ( D C C) a nd 1 ,1 mm ol of 4 -( N , N-d i m et hy l a mi n o) p yr -
id in e w e re ad d e d a nd t he so lut i on w a s st i rre d a t roo m t emp e ra t ur e fo r
3
ho u rs . T he s o lut i on w a s f il t ra t ed t o el i mi na t e t he d i cy cl o hex y l ur ea
a n d t he s o lve nt w a s re mo ve d und er v ac uum. T he 4 -[ 4- (a l l yl o x y p he-
ny l) ]p he n yl - 3- (p er fl uo ro- n- a lk y l )p ro p a no a t e ( EC 4 ꢂ EC 8 ) w er e p uri -
f ied by c o lum n c hro m a t og ra p hy ov e r si li ca ge l usi ng d i chl or ome t ha ne
a s t he e lua nt .
1
F o r E C 8 : H N MR ( CD C l =TM S, d p p m , J H z) , 2 , 60 (2 H , CF CH , t t ,
3
2
2
J ¼ 8, 1 J ¼ 18 , 4) , 2 ,9 5 ( 2H , C F C H CH2 , t , J ¼ 8 , 1) , 4 , 63 (2 H ,
2
2
OCH CH CH , d , J ¼ 5 ,3 ) , 5 ,3 2 ( 1H , O C H CH CH , d d , J ¼ 1 0 ,5
2
2
2
2
J ¼ 1, 5 ), 5, 4 7 (1H , O C H C H CH , d d , J ¼ 1 7 ,3 J ¼ 1 , 5) , 6 , 08 (1 H ,
2
2
O C H CHCH , m , J ¼ 1 0, 5 J ¼ 1 7, 3 , J ¼ 5 ,3) , 7 , 00 (2 H , d , J ¼ 8 , 8) ,
2
2
ar
7
,1 5 (2 H , d , J ¼ 8 ,7 ) , 7 ,5 1 ( 2H , d , J ¼ 8 ,8 ), 7 , 58 (2 H , d , J ¼ 8 , 7)
a r
a r
ar
19
F N. M. R. (C D Cl =C FC l , d p p m ) , ꢁ8 2 ( CF , m) , ꢁ1 1 5 .5 [( CF ) , m] ,
3
3
3
2 a
ꢁ
1 23 [( CF ) , , , m] , ꢁ1 24 [ (C F ) , m] , ꢁ1 2 4 .5 [( CF ) , m] , ꢁ1 2 7
2
b c d
2 e
2 f
[
(C F ) , m ] MS ( 70 eV ) m =z ( %) , 4 1 ( 10 0 %), 6 9 (4 1 , 3 %), 7 7 (3 5 , 1 %),
2
g
1
8 5 (2 2, 1 %), 66 0 ( 11 , 6 %) , 7 00 ( 29 , 5 %) .
3. RESULTS AND DISCUSSION
The c ho ice o f t he mo le c ul ar p a ra me t er s of t h is ser ie s of mon om ers w a s
d et e r m ine d fr o m p re vi ou s w or k s d es c ri b ed i n t he l i t era t u re [1 5 , 1 6 ].
The s e c o mp o un ds a re l ist e d i n Fi g ur e 3 . T he cor resp o nd i ng mes o-
m or p hic p ro p e r t ie s a re re p or t ed i n Fi g ure 4. Ea ch mon om ers na med
Ax , Bx , Cx an d D x d i ff er t o ea c h ot h er b y one mol ec ul a r p a ra me t er.
The c o rr e la ti on b et w e en t he ir me so mor p hic p rop ert i es a l lo w s us t o
co n s id e r t he s e ri e s d es cri b ed i n t he p re se n t w ork a nd cod e d EC x.
The va lue ‘‘x ’’, d es c ri b ed i n t he Fi g ure 4 , eq u a l t o 4 , 6 or 8 , cor re sp ond s
t o t he fl uo ri n at e d me t hy l ene uni t s i n t he F- a l ky l t a i l.

2
42=[1 1 9 6 ]
E. T. de Givenchy et al.
F IG URE 3 A lly lic m on o m ers u s ed f o r co mp aris o n [ 1 5 , 1 6] .
F IG URE 4 C ompa ris o n o f t h e L C ra n g es o f t he m e s oph a s e s f o r co m po u nd s
A x , Bx , Cx , Dx et E C ( x ¼ 4 , 6 , 8 ) .

LC Behaviour of Fluorinated Allylic Monomers
24 3=[ 11 97 ]
T A BL E 2 T ran s itio n T e mpe ra t u res f o r M o no m ers O b s er ve d o n H e a t ing f ro m
ꢀ
ꢁ1
D .S .C . ( Sca n n ing R a t e 1 0 C m in )
ꢀ
Tr a n si t io n Te mp er atu r e ( C)
Cp ds
C
S
E
S
A
I
EC 4
EC 6
EC 8
.
.
.
9 9
9 6
9 5
.
.
.
1 4 2
1 4 3
1 4 7
.
.
.
20 5
21 5
23 0
.
.
.
A E
C, c rys t a l, S , S : Sm ec t i c A a n d E r es pe c t ive ly, I, i so t r op ic .
F IG URE 5 Opt ica l po la riz in g m icro g raph dis pla y e d b y E C 8 o n co o lin g f ro m
ꢀ
is ot ro pic me lt : ( a) t e mpe ra t u re 1 26 C , ꢃ3 3 s a me po s it io n o f t h e s a m ple a s in
ꢀ
F ig u re 5b , ( b) t e mpe ra t u reC , 1ꢃ9 38 3.

2
44=[1 1 9 8 ]
E. T. de Givenchy et al.
F IG URE 5C on t in u ed.
He nc e , ECx al ly l ic co mp ou nd s w er e st ud i ed b y P ol a ri zi n g O p t i ca l
M ic r o s co p y (P . O .M . ) a nd D i f f ere nt i a l Sca n ni n g Ca l or i met r y (D . S.C .)
ꢀ
o n he a t ing an d co ol in g w i th a sc ann i ng ra t e of 1 0 C=mi n. O ur a i m
w as t o s tu d y t he me so mo rp h i c p ro p er t ie s of our 4 -[ 4- (a l l y ox y p heny l )] -
p he ny l- 3-( pe r fl uo ro - n-a l k yl ) p ro p an oa t e a nd t o com p a re t here L .C .
d o m ain s w it h p re vi ou s l y sy n t he ti z ed a ll y li c com p oun d s (F i g . 3 ). T he
Po la r iz e d O p t ica l M ic r os co py ( PO M ) st ud i es show e d t ha t EC 4 t o
EC8 e xh ibi t a sm ec t og e nic t he rmo t rop i c m eso mor p hi sm. T he p h a se
t ra ns i t io n t e m p e ra t ure s a r e g iv e n i n Ta b le 2 .
W e c an no t ic e a w i de me so mo rp hi c sm ect og eni c ra ng e. F rom mi sc i -
b ili ty s tu d ie s w i t h i nt erna l re fe re nce s p re vi ou sl y p ub l i shed [1 0 ], t he
a s sig nm e nt o f m es op ha se s i s of t y p e Sme ct i c E a nd A (se e F ig s. 5 a
a nd 5b ). T ra ns iti o n t em p er a tu re se em s t o b e a s a func t i on of t he num-
b e r o f fl uo ro m e t hy l ene uni t s. Incr ea si ng t he sem i fl uor i na t ed cha i n

LC Behaviour of Fluorinated Allylic Monomers
24 5=[ 11 99 ]
F IG URE 6 I nf lu en ce t h e f lu o rin at e d ch a in s le n g t h s o n t h e m e s om o rph ic
pr o per tie s .
le n gt h, d o e s no t ca use a si g nif i c a nt v ar ia t i o n of t he mel t i ng t emp e ra -
t u r e bu t le a d s t o t he ri se of t he cl ea ri n g p oi nt . T he com p a ri son of t he
LC r ang e ag ai ns t f luo ri n a t ed t a il s l eng t h i s mor e com p l ex . I nd e ed , i f
ꢀ
ꢀ
t h e gl o b al L . C . ra ng e i ncre a s es f rom 1 06 C fo r EC 4 t o 1 3 5 C fo r
EC 8 , t he fl uo ri na t ed cha i n l eng t h d oe s no t show a ny i n fl uen ce on
ꢀ
ꢀ
t h e fi rs t m e so p ha se ( fr om 9 5 t o 1 47 f or a l l com p ound s) w hi l e t he
sme c t ic A p ha s e i ncre a s es w i th t he num ber of p erf lu orom et hy l ene
uni t s (s e e F ig. 6 ). The i ncre a s i ng of f luo ri n at e d t a i l fa v ou ra b l y a ff ec t s
t h e c le ar ing p o int .
W e c an c o mp a re ou r st r uct ure s t o t ho se p rev i ous l y sy nt het i z ed a s
a l ly lic m o no m e r s a na l og ue s a nd p re sen t ed i n F ig ur es 3 a nd 4 . T w o
m es o p ha se s ar e ob se rv e d f or b i p he nyl d er iv at i v es com p oun d s (A a nd
EC ). T he m e so g eni c co re i s a n i mp or t a nt el eme nt fo r t he a p p a ri t i on
o f s e ve r al la rg e a nd mo re or g ani z e me so p hase s. I n cont r as t t o A, t he
li q uid c ry s ta l r ang e of E C mo nom er s i ncre a s es w i t h t he fl uor i na t ed
ch ai n le ng t h. T he w i d es t me so mor p hi c ra ng e w a s ob t a i ned fro m EC
se rie s .
CONCLUSION
The s yn t he s is of a se ri e s o f a l l yl i c mo nom ers d i ffe ri n g onl y b y t he
le n gt h o f t he p e rf l uoro a lk y l t a il ha s b ee n re a l iz ed . Al l mem b e rs of t hi s

2
4 6=[1 2 0 0 ]
E. T. de Givenchy et al.
se r ie s e xh i bi t li q ui d cr ys ta l li n e p h a se of t yp e sme ct ic A a nd E. T he
mo le c ula r c o nce p t i on of t he se mo n om er s f ro m ho mol og o us com p ound s
p re vio u s ly d e sc r ib e d i n t he l it e ra t ure a ll ow s us t o rea ch d i mor p hi sm
a nd w id e r ange sm ect i c me so mo rp hi sm . Thi s ki nd of st r uct ure i s of
a g r e at in t e re s t f or p re curs or of si d e cha i n l i qui d cry st a l l i ne p ol y mer s.
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