ABSTRACT

A new series of push pull azo-dyes containing tricyanodiphenyl electron-withdrowing block, namely (4-N,Ndialkylaminophenyl) azobiphenyl-2,3 ,4 -tricarbonitriles, was proposed and synthesized. The azo-dyes possess high temperature stability and are prone to form polymorph modifications. DSC measurements indicated solidphase transitions of these polymorphs. X-ray diffraction (XRD) analysis revealed that in all solved structures, there is a network of short intermolecular contacts between HArom atoms and N atoms of cyano groups. The supramolecular structure of these contacts depends on the alkyl chain length in the aniline moiety, and changes after temperature induced phase transitions.

Compounds

#	Formula	Name
1	C25H20N6	4-((4-(diethylamino)phenyl)diazenyl)-[1,1'-biphenyl]-2,3',4'-tricarbonitrile
2	C37H44N6	4-((4-(dioctylamino)phenyl)diazenyl)-[1,1'-biphenyl]-2,3',4'-tricarbonitrile
3	C29H28N6	4-((4-(dibutylamino)phenyl)diazenyl)-[1,1'-biphenyl]-2,3',4'-tricarbonitrile
4	C29H28N6	6-((4-(dibutylamino)phenyl)diazenyl)-[1,1'-biphenyl]-2,3',4'-tricarbonitrile
5	C29H29N5O2	5-((4-(dibutylamino)phenyl)diazenyl)-2-(1,3-dioxoisoindolin-5-yl)benzonitrile
6	C15H8N4	4-amino-[1,1'-biphenyl]-2,3',4'-tricarbonitrile
7	C15H6N4O2	4-nitro-[1,1'-biphenyl]-2,3',4'-tricarbonitrile
8	C15H7N3O4	2-(1,3-dioxoisoindolin-5-yl)-5-nitrobenzonitrile
9	C15H9N3O2	5-amino-2-(1,3-dioxoisoindolin-5-yl)benzonitrile

Datasets

The table above is generated from the ThermoML associated json file (link above). POMD and RXND refer to PureOrMixture and Reaction Datasets. The compound numbers are included in properties, variables, and phases, if specificied; the numbers refer to the table of compounds on the left.
Type	Compound-#	Property	Variable	Phase	Method	#Points
POMD	1	Mass density, kg/m3 ; Crystal 2	Temperature, K; Crystal 2 Pressure, kPa; Crystal 2	Crystal 2	X-ray diffraction	1
POMD	1	Triple point temperature, K ; Crystal 2		Crystal 2 Crystal 1 Air at 1 atmosphere	DSC	1
POMD	1	Triple point temperature, K ; Crystal 1		Crystal 1 Liquid Air at 1 atmosphere	DSC	1
POMD	1	Molar enthalpy of transition or fusion, kJ/mol ; Crystal 2		Crystal 2 Crystal 1 Air at 1 atmosphere	DSC	1
POMD	1	Molar enthalpy of transition or fusion, kJ/mol ; Crystal 1		Crystal 1 Liquid Air at 1 atmosphere	DSC	1
POMD	1	Triple point temperature, K ; Metastable crystal		Metastable crystal Liquid Air at 1 atmosphere	DSC	1
POMD	2	Mass density, kg/m3 ; Metastable crystal	Temperature, K; Metastable crystal Pressure, kPa; Metastable crystal	Metastable crystal	X-ray diffraction	1
POMD	2	Triple point temperature, K ; Crystal 1		Crystal 1 Liquid Air at 1 atmosphere	DSC	1
POMD	2	Triple point temperature, K ; Metastable crystal		Metastable crystal Liquid Air at 1 atmosphere	DSC	1
POMD	3	Mass density, kg/m3 ; Crystal 1	Temperature, K; Crystal 1 Pressure, kPa; Crystal 1	Crystal 1	X-ray diffraction	1
POMD	3	Triple point temperature, K ; Crystal 1		Crystal 1 Liquid Air at 1 atmosphere	DSC	1
POMD	3	Molar enthalpy of transition or fusion, kJ/mol ; Crystal 1		Crystal 1 Liquid Air at 1 atmosphere	DSC	1
POMD	3	Triple point temperature, K ; Metastable crystal		Metastable crystal Liquid Air at 1 atmosphere	DSC	1
POMD	3	Triple point temperature, K ; Glass		Glass Liquid Air at 1 atmosphere	DSC	1
POMD	4	Mass density, kg/m3 ; Crystal 2	Temperature, K; Crystal 2 Pressure, kPa; Crystal 2	Crystal 2	X-ray diffraction	1
POMD	4	Triple point temperature, K ; Crystal 2		Crystal 2 Crystal 1 Air at 1 atmosphere	DSC	1
POMD	4	Triple point temperature, K ; Crystal 1		Crystal 1 Liquid Air at 1 atmosphere	DSC	1
POMD	4	Molar enthalpy of transition or fusion, kJ/mol ; Crystal 2		Crystal 2 Crystal 1 Air at 1 atmosphere	DSC	1
POMD	4	Molar enthalpy of transition or fusion, kJ/mol ; Crystal 1		Crystal 1 Liquid Air at 1 atmosphere	DSC	1
POMD	5	Mass density, kg/m3 ; Crystal 2	Temperature, K; Crystal 2 Pressure, kPa; Crystal 2	Crystal 2	X-ray diffraction	1
POMD	5	Triple point temperature, K ; Crystal 2		Crystal 2 Crystal 1 Air at 1 atmosphere	DSC	1
POMD	5	Triple point temperature, K ; Crystal 1		Crystal 1 Liquid Air at 1 atmosphere	DSC	1
POMD	5	Molar enthalpy of transition or fusion, kJ/mol ; Crystal 2		Crystal 2 Crystal 1 Air at 1 atmosphere	DSC	1
POMD	5	Molar enthalpy of transition or fusion, kJ/mol ; Crystal 1		Crystal 1 Liquid Air at 1 atmosphere	DSC	1
POMD	6	Triple point temperature, K ; Crystal		Crystal Liquid Air at 1 atmosphere	VISOBS	1
POMD	7	Triple point temperature, K ; Crystal		Crystal Liquid Air at 1 atmosphere	VISOBS	1
POMD	8	Triple point temperature, K ; Crystal		Crystal Liquid Air at 1 atmosphere	VISOBS	1
POMD	9	Triple point temperature, K ; Crystal		Crystal Liquid Air at 1 atmosphere	VISOBS	1

Thermodynamics Research Center / ThermoML | Thermochimica Acta

Solid-phase transitions of polymorphs of 4-(4-N,N-dialkylaminophenyl)azobiphenyl-2,3',4'-tricarbonitriles and their analogues

Selivanova, G.A., Skolyapova, A.D., Dralyuk, R.I., Karpova, E.V., Shundrina, I.K., Bagryanskaya, I. Yu., Amosov, E.V., Basova, T.V., Tretyakov, E.V.

ABSTRACT