N-alkoxy Benzoyloxy Research Articles

SYNTHESIS AND STUDY OF NEW HOMOLOGOUS SERIES: 4-(4’-N-ALKOXY BENZOYLOXY)-NAPTHYL -1-AZO-(2”-METHYL)- 4”-AZO-2”’-METHYL BENZENE

Novel homologous series 4-(4’-n-alkoxy benzoyloxy)- napthyl-1-azo-(2”-methyl)-4”-azo-2”-methyl benzene consisted of 12 members of a series. All the 12 members (ethoxy to hexadecyloxy) are enantiotropically nematogenic without exhibition of any smectogenic character. Transition temperatures and the textures are determinedby an optical polarizing microscopy furnished with a heatingstage. Textures of a nematic phase are threaded or schlieren. Analytical and spectral data supported the molecular structure ofhomologs. Transition curves viz., solid-nematic and nematic-isotropic showing phase behavior of the mesophase in a phase diagrambehave in normal manner. Reversion of transition temperatures is show by N–I transition curve. Hereby, novel series is entirely nematogenic and high to middle ordered melting type. Thus, synthesis of a novel azo ester homologous series is fulfil with a view to understand and establish the effect of molecular structure on Liquid crystal (LC) behaviors of a substance.

Dependence of mesomorphism on terminal polar group in novel azoester series

Novel homologous series 4-(4′-n-alkoxy benzoyloxy) napthyl azo 4″–bromo benzenes, consisted of 11 members of a series. All the 11 members (ethoxy to hexadecyloxy) except hexadecyloxy are only enantiotropically nematogenic without exhibition of any smectogenic character. Transition temperatures and the textures are determined by an optical polarizing microscopy equipped with a heating stage. Textures of a nematic phase are threaded or schlieren. Analytical and spectral data supported the molecular structure of homologs. Transition curves viz., solid-nematic and nematic-isotropic showing phase behavior of the mesophase in a phase diagram behave in normal manner. Alternation of transition temperatures is exhibited by N–I transition curve. Thus, novel series is entirely nematogenic and high ordered melting type. Thus, synthesis of a novel azoester homologous series is carried out with a view to understand and establish the effect of molecular structure on Liquid crystal (LC) behaviors of a substance.

Mesomorphism in chloro substituted isomeric series including chalconyl central bridge

ABSTRACTA novel homologous series of thermotropic liquid crystals α-4-(4′-n-alkoxy benzoyloxy phenyl) β-2″-chloro benzoyl ethylenes have been synthesized and studied with a view to understand and establish the effect of molecular structure on liquid crystal (LC) properties with reference to molecular flexibility in isomeric series with differing positional status of same functional group. Novel homologues series consist of 12 homologues C1 to C16. C1, C2, and C3 homologues are nonliquid crystals (NLC) and rest of the homologues are liquid crystals. C10 to C16 homologues are enantiotropically smectogenic plus nematogenic and C4 to C8 homologues are enantiotropic nematic. The texture of nematogenic derivatives is threaded or schlieren and that of the smectic mesophase are focal conic of the type smectic A or C. Analytical, thermal and spectral data supported molecular structures of novel homologues. Transition temperatures as determine by a hot stage polarizing optical microscopy (POM) were plotted against number of carbon atom present in n-alkyl chain ‘R’ of left n-alkoxy (-OR) group and the phase transition curves Cr–I/M, Sm–N, N–I were obtained on linking like or related points. The odd–even effect is observed for the N–I transition curve and thus transition curves behaved in normal manner. The even-membered nematic transition curve occupied higher position than the odd-membered transition curve. Present series is predominantly nematogenic and partly smectogenic with middle-ordered melting type.

Study of mesomorphism and its relation to molecular structure with special reference to central bridges viz. -COO- and -CH=CH-COO- of the homologous series

GRAPHICAL ABSTRACT

Mesomorphism dependence on lateral substitution of functional groups and their position in series: 4(4′-n-alkoxy benzoyloxy)-3-chloro phenyl azo-2″-methoxy benzenes

ABSTRACTEleven homologues of the title series were synthesized. The methyl-to-pentyl derivatives are nonmesomorphic. The nematic mesophase commences from the sixth member of the series without any smectic phase. An odd–even effect in the nematic–isotropic transition curve is not observed. The nematic mesophase appeared as a threaded or a Schlieren-type texture as observed through a hot-stage polarizing microscope. The nematic–isotropic transition temperatures are between 89°C and 127°C with the mesomorphic range varying from 9°C to 44°C at the hexyl and tetradecyl derivative of the series, respectively. The nematic–isotropic transition curve initially rises and then falls in a normal manner as the series is ascended, but it abnormally rises beyond the 10th homologue. The series is enantiotropic nematic with a middle-ordered melting type. Analytical data support the structures of the molecules. The thermal stability and some other mesomorphic characteristics are compared with structurally similar homologous series. The average nematic–isotropic thermal stability is 105.4°C.

Synthesis and Study of Novel Mesogenic Homologous Series: 4-(4′-n-alkoxy benzoyloxy)-n-propyl Cinnamates

A novel homologous series of liquid crystals viz. 4-(4′-n-alkoxy benzoyloxy) n-propyl cinnamates comprising of 11 homologues has been synthesized. It is a middle ordered melting type of series with exhibition of smectic and nematic mesophases. The first to fifth members of the series are non-mesomorphic. Mesomorphic behavior commences from the sixth homologue. The octyloxy (C8) and decyloxy (C10) homologues are polymesomorphic. The smectic–nematic and nematic–isotropic transition curves behave in a normal manner except for the hexadecyl derivative, which slightly deviates from normal behavior (N–I). An odd–even effect was not observed for the N–I or Sm–N transition curves. The texture of nematic phase is threaded or Schlieren and that of the smectic phase is focal conic fan shaped of the smectic-A type. Transition temperatures and textures of mesophases were observed through an optical polarizing microscope equipped with a heating stage. Thermal stability and mesomorphic characteristics are compared with a structurally related series. Analytical and spectral data support the structure of the molecules.

Synthesis and Characterization of Novel Thermotropic Liquid Crystals with a Lateral Chloro Group

Twelve novel homologues having azolinkage of the series 4-Carbethoxy-[3′chloro-4′ (4″-n-alkoxy benzoyloxy)] azobenzenes has been synthesized. The methyl to n-hexyl homologues exhibit only a nematic mesophase, while the n-heptyl to n-dodecyl homologues exhibit both smectic and nematic mesophases. The n-tetradecyl and n-hexadecyl homologues exhibit only smectic mesophases. The plot of transition temperatures versus number of carbon atoms in alkoxy chain exhibits an odd-even effect for the nematic-isotropic transition temperatures. The mesogenic behavior of present series is explained by comparing its homologue with other homologue of related mesogenic series. The synthesized compounds were characterized by combination of elemental analysis and standard spectroscopic methods. For the exhibition of mesomorphic property the role of ester and azo linkages has been discussed. The impact of lateral chloro group on mesomorphism is also discussed.

Mesomorphism and Molecular Structure of Ester Homologous Series Containing Carboxy and Vinyl Carboxy Linking Groups

A novel homologous series 4-(4′-n-alkoxy benzoyloxy)-isopentyl cinnamates consisting of eleven homologs is reported. Mesomorphism commences from the hexyloxy homolog up to the hexadecyloxy homolog. The hexyloxy and hexadecyloxy derivatives are only enantiotropically nematogenic while, but the octyl, decyl, dodecyl, and tetradecyl homologs exhibit enantiotropic nematogenic and smectogenic mesophases. The rest of the homologs are nonmesogenic. The textures of nematic phase are threaded or Schlieren and that of the smectic mesophase is focal conic smectic A or C type. The transition curves of the phase diagram behave in a normal manner without the exhibition of an odd-even effect. Analytical and spectral data confirm the molecular structure of the homologs. Overall mesogenic phase temperature range varies from 11.0°C to 59.0°C. The average thermal stabilities of smectic and nematic are 122.25°C and 139.0°C, respectively. The series is predominantly nematogenic and partly smectogenic with a middle-ordered melting type and a considerable range of liquid crystallinity. Melting points and transition temperatures were determined using an optical polarizing microscope equipped with a heating stage. The mesomorphic properties are compared with structurally similar series.

Study of Novel Symmetrical Liquid Crystalline Ester Dimers

A novel homologous series of 12 symmetrical dimers, viz. 1,1’-Bis[4-(4’-n-alkoxy benzoyloxy)-3-methyl phenyl] cyclohexanes is reported. Nematogenic mesophase commences from the heptyloxy homologue dimer and continues up to the hexadecyloxy dimer in an enantiotropic manner without the exhibition of any smectogenic behavior. The rest of the dimers from methoxy to hexyloxy are nonmesogenic. The textures of the nematic phase are threaded or Schlieren. The transition temperatures and textures of the nematic phase were determined by an optical polarizing microscope equipped with a heating stage. Curves (solid-isotropic/nematic and N-I) of a phase diagram showing mesomorphism behave in normal manner except for a minor deviation at the dodecyloxy derivative. The analytical and spectral data confirm the molecular structure of dimers. The nematogenic mesophase lengths vary between 3.3°C and 26.6°C. The average thermal stability for nematic is 108.26°C; series is partly nematogenic with middle ordered melting type and low degree of mesomorphism. Liquid crystal properties of novel dimer series are compared with the structurally similar other known series.

Mesomorphism Dependence on Terminal/Lateral Substitution of Nonlinear Azoester Molecules

A novel azo ester homologous series of liquid crystals (LCs) 2(4′-n-alkoxy benzoyloxy) napthyl 1 azo-3″ nitrobenzenes consists of eleven members of a series with enantiotropic nematogenic mesophase formation and without exhibition of smectogenic property by all the eleven homologs. The nematogenic mesophase textures are threaded or Schlieren. Solid-nematic and nematic-isotropic transition curves of the phase diagram behave in normal manner except for the decyloxy, dodecyloxy, and tetradecyloxy homologs. Analytical and spectral data confirm the molecular structures of homologues. Thermal stability for the nematic phase is 132.6°C, and the degree of mesomorphism varies between 34°C and 79°C and the series if of a middle-ordered melting type. An odd-even effect is observed for the N-I transition curve with alternation of transition temperatures. The LC behavior of the series is compared with other structurally similar known homologous series to establish the relation between mesomorphism and molecular structure.

Mesomorphism Dependence on Molecular Flexibility by –OCH3 and –H Terminal Units

A novel ester homologous series: 4-(4’-n-Alkoxy benzoyloxy)-4”-methoxy benzyl cinnamates have been synthesized and studied with a view to understanding and establishing the dependence of liquid crystal behavior on molecular structure. The novel series of eleven homologues is entirely nematogenic without exhibition of any smectogenic character from the very first member of the series. Transition and melting temperatures were determined by an optical polarizing microscopy equipped with a heating stage. Transition curves of a phase diagram show the mesomorphism, which behaves in normal manner. An odd-even effect is exhibited by the nematic–isotropic transition curve. The textures of the nematic mesophase are threaded or schlieren in type. Analytical and spectral data confirm the molecular structures of the novel homologues. Thermal stability for the nematic phase is 211.5°C and the degree of mesomorphism varies from 17°C to 72°C and it is a high melting type series. Mesomorphic properties of the series are compared with structurally similar series.

Mesomorphism Dependence on Positional Substitution of Same Polar Group on Same Phenyl Ring in Isomeric Homologous Series

Novel homologous series 4-(4′-n-alkoxy benzoyloxy) napthyl azo 2′′ – nitro benzenes, consisted of eleven members of a series. All the eleven members (methoxy to tetradecyloxy) homologs are only enantiotropically nematogenic without exhibition of any smectogenic character. Transition temperatures and the textures are determined by an optical polarizing microscopy equipped with a heating stage. Textures of a nematic phase are threaded or schlieren. Analytical and spectral data supported the molecular structure of homologs. Transition curves viz., solid-nematic and nematic-isotropic showing phase behavior of the mesophase in a phase diagram behave in normal manner. Odd-even effect and alternation of transition temperatures are exhibited by N-I transition curve. N-I thermal stability is 129.7°C and Nematic mesophase vary from 12 to 64°C. Thus, novel series is entirely nematogenic and middle ordered melting type. Mesomorphic behavior of a novel series are compared with the structurally similar homologous series.

Effect of a Central Group on Mesomorphism

A novel homologous series: 4-(4′-n-alkoxy benzoyloxy)-4″-methoxy benzyl benzoates is studied with a view to understanding the effect of a central group on the phenomenon of mesomorphism. The novel homologous series consists of eleven compounds. Mesomorphism commences from the second member of a series. All the mesogenic homologues from ethoxy to hexadecyloxy exhibit nematogenic mesomorphism without the exhibition of smectogenic character. The nematic–isotropic transition curve of the phase diagram behaves in normal manner up to the dodecyloxy homologue and then deviated for the tetradecyloxy and hexadecyloxy homologues. The solid-isotropic or nematic transition curve adopts a normal behavior in a zigzag manner. The nematic-isotropic transition curve shows an odd-even effect and continues up to the octyloxy homologue. Transition and melting temperatures including the textures of mesophases are determined by an optical polarizing microscope, equipped with a heating stage. The textures of the nematic mesophase are threaded or Schlieren in type. Analytical data and spectral data support the molecular structures. The mesomorphic behavior of the present series is compared with structurally similar other known series of differing central group (viz. ‒N˭N‒ and ‒CO‒CH˭CH‒) keeping rest of a molecular part unchanged. The nematic thermal stability of the series is 236.8°C of a high melting type present series whose nematogenic mesophase length varies between 27°C and 98°C. Thus, series is only nematogenic without exhibition of a smectic mesophase.

The Relation Between Mesomorphism and Molecular Structure of a Novel Azoester Series Involving Laterally Substituted Chloro Groups

A novel azoester homologous series 4-(4′-n-alkoxy benzoyloxy) phenyl azo 2″,6″-dichloro benzene is synthesized and studied with a view to understand and establish the effects of molecular structure on liquid crystal behavior of a substance with reference to steric hindrance. The novel homologous series consists of twelve homologues. Mesomorphism commences from the heptyloxy homologue and continues up to the hexadecyloxy homologue as a monotropic nematic without the exhibition of any smectogenic characteristics. Transition temperatures were determined by an optical polarizing microscopy equipped with a heating stage. Transition curves of the phase diagram behave in a normal manner. The isotropic-nematic transition curve shows an odd-even effect in the very short range of temperature. The texture of nematic mesophase is threaded. Analytical and spectral data support the molecular structures of the homologues. Thermal stability is very low and the degree of mesomorphism is poor. Thus novel series is of low melting type and nematogenic only in a monotropic manner. Mesomorphic properties of the present, novel series are compared with structurally similar other known series.

Mesomorphism in Relation to Molecular Structure with Reference to a Laterally Substituted Homologous Series

A novel homologous series 4-(4′-n-alkoxy benzoyloxy) 3-methyl phenyl azo-2″, 6″-dimethyl benzenes consists of 12 homologues. The methyl to hexyl derivatives are non-mesomorphic and the rest of the homologues are mesomorphic. Mesomorphism commences from heptyl homologue in a monotropic manner and continues as an enantiotropic nematic for octyl to dodecyl derivatives, and then monotropic mesomorphism as a nematic mesophase reappears for tetradecyl and hexadecyl derivatives without the exhibition of smectogenic character. The textures of the nematic mesophase are threaded, or are schlieren in type. The nematic–isotropic (or vice versa) transition curve of the phase diagram behaves in a normal manner without the exhibition of an odd-even effect. The average thermal stability for nematic to isotropic transition is 126.5°C. Analytical and spectral data confirm the structure of molecules. The mesomorphic to isotropic transition temperatures vary between 56°C and 130°C. The nematogenic mesophase appeared at the lowest temperature of 41.3°C. Transition and melting temperatures are determined using an optical polarizing microscopy equipped with a heating stage. The present novel series is of a low ordered melting type and predominantly nematogenic, without the exhibition of smectogenic character.

Synthesis and Mesomorphic Properties of a Novel Ester Homologous Series: 4-(4′-n-Alkoxy Benzoyloxy) Benzyl Cinnamates

A novel homologous series 4-(4′-n-alkoxy benzoyloxy) benzyl cinnamates was synthesized and studied with a view to understanding and establishing the relationships between mesomorphism and molecular structure. The novel series consists of eleven members with the commencement of mesomorphism from the pentyloxy homologue onwards to the hexadecyl homologue. The remaining homologues are nonmesomorphic. All the mesomorphic homologues exhibit smectogenic mesomorphism in addition to nematogenic mesomorphism for a definite temperature range in an enantiotropic manner, except for the pentyloxy homologue, which exhibits only a nematogenic mesophase in an enantiotropic manner without the formation of a smectic phase. The texture of the nematic mesophase is of the threaded or Schlieren type and the smectic mesophase is of the type A or C texture, as determined by a miscibility method. Transition temperatures were observed through an optical polarizing microscope equipped with a heating stage. The transition curves of a phase diagram predominantly behave in a normal manner, but partly deviated from normal behavior with the exhibition of an odd–even effect. Analytical and spectral data confirms the molecular structures of all homologues. The mesomorphic behavior of the present series is compared with other structurally similar known series. The mesomorphic temperatures vary between 106°C and 180°C. The mesophase length varies between 33°C to 53°C. Thus, the novel series is predominantly nematogenic and partly smectogenic with relatively high transition temperatures and is of a high melting type. The average thermal stabilities for smectic and nematic phases are 144.1°C and 171.4°C, respectively.

Study of Mesomorphism Through a Novel Homologous Series and Its Relation to Molecular Structure

A novel homologous series 4-(4′-n-alkoxy benzoyloxy)-3-chloro phenyl azo,3″,4″-dichlorobenzenes was synthesized with a view to understand and establish the relation between mesomorphism and the molecular structure. The novel series consists of 12 members, which showed commencement of monotropic nematic mesophase formation from the butoxy homologue and continued up to the hexadecyloxy homologue without exhibition of a smectic mesophase. The textures of the nematic mesophase are threaded or Schlieren in type. Transition temperatures were determined by an optical polarizing microscope equipped with a heating stage. Isotropic-nematic transition curve of the phase diagram behaved in normal manner with exhibition of odd-even effect. Solid-isotropic transition curve behaved descending tendency by adopting zigzag path up to the pentyloxy homologue; which include methoxy to propoxy homologues as nonmesomorphic derivatives. Thermal stability for the nematic is just a few degrees (1°C to 2°C). Analytical and spectral data support the molecular structures. The mesomorphic properties of present novel series are compared with structurally similar other known homologous series.

Synthesis and Evaluation of Liquid Crystal Behavior of a Novel Homologous Series: 4-(4′-n-Alkoxy benzoyloxy) Phenylazo-2″, 6″-dimethylbenzenes

A novel homologous series entitled 4-(4′-n-alkoxy benzoyloxy) phenyl azo 2″, 6″-dimethyl benzenes consisting of 12 members is reported. Liquid crystal behavior as a nematogenic mesophase commences from the pentyloxy homologue monotropically and then continues enantiotropically until the last hexadecyloxy homologue without exhibition of any smectogenic behavior. An odd-even effect is observed for nematic-isotropic transition curve of the phase diagram. The textures of the nematic mesophase are of the threaded or Schlieren type. Analytical and spectral data support the molecular structure of the homologues. Transition temperatures of the novel homologues were determined by an optical polarizing microscopy. Liquid crystal properties of a novel homologous series are compared with other known homologous series. The average thermal stability for the nematic phase is 77.1°C.

Synthesis and Liquid Crystal Properties of a Novel Homologous Series 4-(4′-n-Alkoxy benzoyloxy) Benzyl Benzoates

A novel homologous series consisting of 11 homologues is reported. Liquid crystal properties commence from the hexyloxy homologue and continue up to the tetradecyloxy homologue as enantiotropic nematic mesomorphism only. The rest of the homologues (including hexadecyloxy homologue) are not liquid crystalline. None of the homologues show smectogenic mesophase formation. The texture of the nematic mesophase is of a threaded or Schlieren type. The transition temperatures of the homologues were determined by optical polarizing microscopy equipped with a heating stage. Transition curves of a phase diagram behave in normal manner except for the tetradecyloxy homologue which adopts an unexpected trend of propagation. An odd–even effect is absent for nematic-isotropic transition curve. Analytical and spectral data support the molecular structure of the homologues. The average thermal stability of the series is 78.8°C. Mesomorphic/nematogenic phase length varies from 2.0°C to 13.0°C. The liquid crystal behavior of the present series is compared with structurally similar other known series. Thus, the present series is enantiotropically nematogenic only without exhibition of any smectogenic character with a low melting type, whose mesomorphic phase length is relatively short.

Synthesis and Mesomorphic Phase Behavior of Laterally Substituted Novel Azoesters

A novel homologous series of 4(4′-n-alkoxy benzoyloxy)phenylazo 2′′-chloro-3′′-methyl benzenes was synthesized and studied for mesophase behavior dependence on molecular structure. The nematogenic mesophase is exhibited from the first to the last member and the smectogenic mesophase from the hexyloxy to the tetradecyloxy member of the series. The nematic mesophase is of a threaded or Schlieren type, and the smectic mesophase is of a focal conic fan of the type A or C. Mesomorphic properties of the present novel homologous series are compared with other structurally similar homologous series.