Method for the preparation of thin large-area single crystals of diacetylenes and polydiacetylenes

Claim 1

A method for preparing thin large-area single crystals of a diacetylene monomer comprising: forming a liquid layer containing molten pure diacetylene monomer represented by the formula R--C.tbd.C--C.tbd.C--R' wherein R and R' are side groups selected such that the diacetylene monomer is polymerizable by a 1,4-addition solid state reaction upon exposure to actinic radiation between two clean, parallel, flat, smooth, opposed surfaces; applying pressure of at least 0.5 psi to the liquid layer disposed between the two opposed surfaces; and crystallizing the liquid layer disposed between the two opposed surfaces, while the liquid layer is kept under constant pressure of at least 0.5 psi, to form a thin large-area single crystal of diacetylene monomer; wherein the steps of forming, applying pressure to, and crystallizing the liquid layer are all carried out in an inert atmosphere.

Claim 2

A method for preparing thin large-area single crystals of a diacetylene monomer comprising: forming a liquid layer containing molten pure diacetylene monomer represented by the formula R--C.tbd.C--C.tbd.C--R' wherein R and R' are side groups selected such that the diacetylene monomer is polymerizable by a 1,4-addition solid state reaction upon exposure to actinic radiation between two clean, parallel, flat, smooth, opposed surfaces; applying pressure of at least 0.5 psi to the liquid layer disposed between the two opposed surfaces; and crystallizing the liquid layer disposed between the two opposed surfaces, while the liquid layer is kept under constant pressure of at least 0.5 psi, to form a thin large-area single crystal of diacetylene monomer; wherein the steps of forming, applying pressure to, and crystallizing the liquid layer are all carried out in an inert atmosphere.

Claim 4

A method for preparing thin large-area single crytals of diacetylene monomer comprising: forming a liquid layer containing pure diacetylene monomer represented by the formula R--C.tbd.C--C.tbd.C--R' wherein R and R' are selected from the group R and R' pairs consisting of R=--CH 2 OSO 2 C 6 H 4 CH 3 and R'=--CH 2 OSO 2 C 6 CH 3 ; R=--CH 2 OCONHC 6 H 5 and R'=--CH 2 OCONHC 6 H 5 ; R=--(CH 2 ) 3 OCONHC 6 H 5 and R'=--(CH 2 ) 3 OCONHC 6 H 5 ; R=--(CH 2 ) 4 OCONHC 6 H 5 and R'=--(CH 2 ) 4 OCONHC 6 H 5 ; R=--(CH 2 ) 4 OCONHC 2 H 5 and R'=--(CH 2 ) 4 OCONHC 2 H 5 ; R=--(CH 2 ) 4 OCONHCH(CH 3 ) 2 and R'--(CH 2 ) 4 OCONHCH(CH 3 ) 2 ; R=--(CH 2 ) n OCONHCH 2 COOZ and R'=--(CH 2 ) n OCONHCH 2 COOZ, wherein Z is an alkyl or aryl group; R=--CH 2 NC 12 H 8 and R'=--CH 2 NC 12 H 8 ; R=--(CH 2 ) 2 OH and R'=--(CH 2 ) 2 OH; R=--(CH 2 ) 3 OH and R'=--(CH 2 ) 3 OH; R=--(CH 2 ) 8 COOCH 3 and R'=--(CH 2 ) 8 COOCH 3 ; R=--CH 2 OH and R'=--CH 3 ; R=--(CH 2 ) n CH 3 and R'=--(CH 2 ) m COOH, wherein 12<n<16, 1<m<10, and n and m are different integers; and R=--(CH 2 ) n CH 3 and R'=--(CH 2 ) m COO - Li + , wherein 12<n<16, 1<m<10, and n and m are different integers; between two clean, parallel, flat, smooth, opposed surfaces by melting the pure diacetylene monomer between the two opposed surfaces to form a molten diacetylene monomer layer between the two opposed surfaces; applying pressure greater than or equal to approximately 0.5 psi to the liquid layer disposed between the two opposed surfaces; and crystallizing the liquid layer disposed between the two opposed surfaces, while the liquid layer is kept under constant pressure of at least 0.5 psi, by cooling the molten diacetylene monomer layer at a rate less than or equal to about 0.1° C./minute to form a thin large-area single crystal diacetylene monomer; wherein the step of forming, applying pressure to, and crystallizing the liquid layer are all carried out in an inert atmosphere.

Claim 5

A method for preparing thin large-area single crytals of diacetylene monomer comprising: forming a liquid layer containing pure diacetylene monomer represented by the formula R--C.tbd.C--C.tbd.C--R' wherein R and R' are selected from the group R and R' pairs consisting of R=--CH 2 OSO 2 C 6 H 4 CH 3 and R'=--CH 2 OSO 2 C 6 CH 3 ; R=--CH 2 OCONHC 6 H 5 and R'=--CH 2 OCONHC 6 H 5 ; R=--(CH 2 ) 3 OCONHC 6 H 5 and R'=--(CH 2 ) 3 OCONHC 6 H 5 ; R=--(CH 2 ) 4 OCONHC 6 H 5 and R'=--(CH 2 ) 4 OCONHC 6 H 5 ; R=--(CH 2 ) 4 OCONHC 2 H 5 and R'=--(CH 2 ) 4 OCONHC 2 H 5 ; R=--(CH 2 ) 4 OCONHCH(CH 3 ) 2 and R'--(CH 2 ) 4 OCONHCH(CH 3 ) 2 ; R=--(CH 2 ) n OCONHCH 2 COOZ and R'=--(CH 2 ) n OCONHCH 2 COOZ, wherein Z is an alkyl or aryl group; R=--CH 2 NC 12 H 8 and R'=--CH 2 NC 12 H 8 ; R=--(CH 2 ) 2 OH and R'=--(CH 2 ) 2 OH; R=--(CH 2 ) 3 OH and R'=--(CH 2 ) 3 OH; R=--(CH 2 ) 8 COOCH 3 and R'=--(CH 2 ) 8 COOCH 3 ; R=--CH 2 OH and R'=--CH 3 ; R=--(CH 2 ) n CH 3 and R'=--(CH 2 ) m COOH, wherein 12<n<16, 1<m<10, and n and m are different integers; and R=--(CH 2 ) n CH 3 and R'=--(CH 2 ) m COO - Li + , wherein 12<n<16, 1<m<10, and n and m are different integers; between two clean, parallel, flat, smooth, opposed surfaces by melting the pure diacetylene monomer between the two opposed surfaces to form a molten diacetylene monomer layer between the two opposed surfaces; applying pressure greater than or equal to approximately 0.5 psi to the liquid layer disposed between the two opposed surfaces; and crystallizing the liquid layer disposed between the two opposed surfaces, while the liquid layer is kept under constant pressure of at least 0.5 psi, by cooling the molten diacetylene monomer layer at a rate less than or equal to about 0.1° C./minute to form a thin large-area single crystal diacetylene monomer; wherein the step of forming, applying pressure to, and crystallizing the liquid layer are all carried out in an inert atmosphere.

Claim 6

A method for preparing thin large-area single crystals of diacetylene monomer comprising: forming a liquid layer containing pure diacetylene monomer represented by the formula R--C.tbd.C--C.tbd.C--R' wherein R and R' are side groups selected such that the diacetylene monomer is polymerizable by a 1,4-addition solid state reaction upon exposure to actinic radiation between two clean, parallel, flat, smooth, opposed surfaces by melting thepure diacetylene monomer between the two opposed surfaces to form a molten diacetylene monomer layer; applying pressure greater than or equal to about 0.5 psi to the liquid layer disposed between the two opposed surfaces; and crystallizing the liquid layer disposed between the two opposed surfaces, while the liquid layer is kept under constant pressure of at least 0.5 psi, by cooling the molten diacetylene monomer layer at a cooling rate less than or equal to about 0.1° C./minute to form a thin large-area single crystal of diacetylene monomer; wherein the step of forming, applying pressure to, and crystallizing the liquid layer are all carried out in an inert atmosphere.

Claim 7

A method for preparing thin large-area single crystals of diacetylene monomer comprising: forming a liquid layer containing pure diacetylene monomer represented by the formula R--C.tbd.C--C.tbd.C--R' wherein R and R' are side groups selected such that the diacetylene monomer is polymerizable by a 1,4-addition solid state reaction upon exposure to actinic radiation between two clean, parallel, flat, smooth, opposed surfaces by melting thepure diacetylene monomer between the two opposed surfaces to form a molten diacetylene monomer layer; applying pressure greater than or equal to about 0.5 psi to the liquid layer disposed between the two opposed surfaces; and crystallizing the liquid layer disposed between the two opposed surfaces, while the liquid layer is kept under constant pressure of at least 0.5 psi, by cooling the molten diacetylene monomer layer at a cooling rate less than or equal to about 0.1° C./minute to form a thin large-area single crystal of diacetylene monomer; wherein the step of forming, applying pressure to, and crystallizing the liquid layer are all carried out in an inert atmosphere.

Claim 10

A method for preparing thin large-area single crystals of polydiacetylene comprising: forming a liquid layer containing molten pure diacetylene monomer represented by the formula R--C.tbd.C--C.tbd.C--R' wherein R and R' are side groups selected such that the diacetylene monomer is polymerizable by a 1,4-addition solid state reaction upon exposure to actinic radiation between two clean, parallel, flat, smooth, opposed surface; applying pressure of at least 0.5 psi (0.04 kg.cm -2 ) to the liquid layer disposed between the two opposed surfaces; and crystallizing the liquid layer disposed between the two opposed surfaces, while the liquid layer is kept under constant pressure of at least 0.5 psi, to a form a thin large-area single crystal of diacetylene monomer; and exposing the thin large-area single crystal of diacetylene monomer to ultraviolet or gamma radiation to form a thin large-area single crystal of polydiacetylene; wherein the steps of forming, applying pressure to, and crystallizing the liquid layer and exposing the monomer to radiation are all carried out in an inert atmosphere.

Claim 11

A method for preparing thin large-area single crystals of polydiacetylene comprising: forming a liquid layer containing molten pure diacetylene monomer represented by the formula R--C.tbd.C--C.tbd.C--R' wherein R and R' are side groups selected such that the diacetylene monomer is polymerizable by a 1,4-addition solid state reaction upon exposure to actinic radiation between two clean, parallel, flat, smooth, opposed surface; applying pressure of at least 0.5 psi (0.04 kg.cm -2 ) to the liquid layer disposed between the two opposed surfaces; and crystallizing the liquid layer disposed between the two opposed surfaces, while the liquid layer is kept under constant pressure of at least 0.5 psi, to a form a thin large-area single crystal of diacetylene monomer; and exposing the thin large-area single crystal of diacetylene monomer to ultraviolet or gamma radiation to form a thin large-area single crystal of polydiacetylene; wherein the steps of forming, applying pressure to, and crystallizing the liquid layer and exposing the monomer to radiation are all carried out in an inert atmosphere.

Claim 13

A method for preparing thin large-area single crystals of polydiacetylene comprising: forming a liquid layer containing pure diacetylene monomer represented by the formula: R--C.tbd.C--C.tbd.C--R' wherein R and R' are selected from the group R and R' pairs consisting of R=--CH 2 OSO 2 C 6 H 4 CH 3 and R'=--CH 2 OSO 2 C 6 H 4 CH 3 ; R=--CH 2 OCONHC 6 H 5 and R'=--CH 2 OCONHC 6 H 5 ; R=--(CH 2 ) 3 OCONHC 6 H 5 and R'=--(CH 2 ) 3 OCONHC 6 H 5 ; R=--(CH 2 ) 4 OCONHC 6 H 5 and R'=--(CH 2 ) 4 OCONHC 6 H 5 ; R=--(CH 2 ) 4 OCONHC 2 H 5 and R'=--(CH 2 ) 4 OCONHC 2 H 5 ; R=--(CH 2 ) 4 OCONHCH(CH 3 ) 2 and R'=--(CH 2 ) 4 OCONHCH(CH 3 ) 2 ; R=--(CH 2 ) n OCONHCH 2 COOZ and R'=--(CH 2 ) n OCONHCH 2 COOZ, wherein Z in an alkyl or aryl group; R=--CH 2 NC 12 H 8 and R'=--CH 2 NC 12 H 8 ; R=--(CH 2 ) 2 OH and R'=--(CH 2 ) 2 OH; R=--(CH 2 ) 3 OH and R'=--(CH 2 ) 3 OH; R=--(CH 2 ) 8 COOCH 3 and R'=--(CH 2 ) 8 COOCH 3 ; R=--CH 2 OH and R'=--CH 3 ; R=--(CH 2 ) n CH 3 and R'=--(CH 2 ) m COOH, wherein 12<n<16, 1<m<10, and n and m are different integers; and R=--(CH 2 ) n CH 3 and R'=--(CH 2 ) m COO - Li + , wherein 12<n<16, 1<m<10, and n and m are different integers; between two clean, parallel, flat, smooth, opposed surfaces by melting the pure diacetylene monomer between the two opposed surfaces to form a molten diacetylene monomer layer between the two opposed surfaces; applying pressure greater than or equal to approximately 0.5 psi to the liquid layer disposed between the two opposed surfaces; and crystallizing the liquid layer disposed between the two opposed surfaces, while the liquid layer is kept under constant pressure of at least 0.5 psi, by cooling the molten diacetylene monomer layer at a cooling rate less than or equal to about 0.1° C./minute to form a thin large-area single crystal of diacetylene monmer; and exposing the thin large-area single crystal of diacetylene monomer to actinic radiation to form a thin large-area single crystal of polydiacetylene; wherein the steps of forming, applying pressure to, and crystallizing the liquid layer and exposing the monomer to radiation are all carried out in an inert atmosphere.

Claim 14

A method for preparing thin large-area single crystals of polydiacetylene comprising: forming a liquid layer containing pure diacetylene monomer represented by the formula: R--C.tbd.C--C.tbd.C--R' wherein R and R' are selected from the group R and R' pairs consisting of R=--CH 2 OSO 2 C 6 H 4 CH 3 and R'=--CH 2 OSO 2 C 6 H 4 CH 3 ; R=--CH 2 OCONHC 6 H 5 and R'=--CH 2 OCONHC 6 H 5 ; R=--(CH 2 ) 3 OCONHC 6 H 5 and R'=--(CH 2 ) 3 OCONHC 6 H 5 ; R=--(CH 2 ) 4 OCONHC 6 H 5 and R'=--(CH 2 ) 4 OCONHC 6 H 5 ; R=--(CH 2 ) 4 OCONHC 2 H 5 and R'=--(CH 2 ) 4 OCONHC 2 H 5 ; R=--(CH 2 ) 4 OCONHCH(CH 3 ) 2 and R'=--(CH 2 ) 4 OCONHCH(CH 3 ) 2 ; R=--(CH 2 ) n OCONHCH 2 COOZ and R'=--(CH 2 ) n OCONHCH 2 COOZ, wherein Z in an alkyl or aryl group; R=--CH 2 NC 12 H 8 and R'=--CH 2 NC 12 H 8 ; R=--(CH 2 ) 2 OH and R'=--(CH 2 ) 2 OH; R=--(CH 2 ) 3 OH and R'=--(CH 2 ) 3 OH; R=--(CH 2 ) 8 COOCH 3 and R'=--(CH 2 ) 8 COOCH 3 ; R=--CH 2 OH and R'=--CH 3 ; R=--(CH 2 ) n CH 3 and R'=--(CH 2 ) m COOH, wherein 12<n<16, 1<m<10, and n and m are different integers; and R=--(CH 2 ) n CH 3 and R'=--(CH 2 ) m COO - Li + , wherein 12<n<16, 1<m<10, and n and m are different integers; between two clean, parallel, flat, smooth, opposed surfaces by melting the pure diacetylene monomer between the two opposed surfaces to form a molten diacetylene monomer layer between the two opposed surfaces; applying pressure greater than or equal to approximately 0.5 psi to the liquid layer disposed between the two opposed surfaces; and crystallizing the liquid layer disposed between the two opposed surfaces, while the liquid layer is kept under constant pressure of at least 0.5 psi, by cooling the molten diacetylene monomer layer at a cooling rate less than or equal to about 0.1° C./minute to form a thin large-area single crystal of diacetylene monmer; and exposing the thin large-area single crystal of diacetylene monomer to actinic radiation to form a thin large-area single crystal of polydiacetylene; wherein the steps of forming, applying pressure to, and crystallizing the liquid layer and exposing the monomer to radiation are all carried out in an inert atmosphere.

Claim 15

A method for preparing thin large-area single crystals of polydiacetylene comprising: forming a liquid layer containing pure diacetylene monomer represented by the formula R--C.tbd.C--C.tbd.C--R' wherein R and R' are side groups selected such that the diacetylene monomer is polymerizable by a 1,4-addition solid state reaction upon exposure to actinic radiation between two clean, parallel, flat, smooth, opposed surfaces by melting the pure diacetylene monomer between the two opposed surfaces to form a molten diacetylene monomer layer; applying pressure greater than or equal to about 0.5 psi to the liquid layer disposed between the two opposed surfaces; crystallizing the liquid layer disposed between the two opposed surface, while the liquid layer is kept under constant pressure of at least 0.5 psi, by cooling the molten diacetylene monomer layer at a cooling rate less than or equal to about 0.1° C./minute to form thin large-area single crystal of diacetylene monomer; and exposing the thin large-area single crystal of diacetylene monomer to ultraviolet or gamma radiation to form a thin large-area single crystal of polydiacetylene; wherein the steps of forming, applying pressure to, and crystallizing the liquid layer and exposing the monomer to radiation are all carried out in an inert atmosphere.

Claim 16

A method for preparing thin large-area single crystals of polydiacetylene comprising: forming a liquid layer containing pure diacetylene monomer represented by the formula R--C.tbd.C--C.tbd.C--R' wherein R and R' are side groups selected such that the diacetylene monomer is polymerizable by a 1,4-addition solid state reaction upon exposure to actinic radiation between two clean, parallel, flat, smooth, opposed surfaces by melting the pure diacetylene monomer between the two opposed surfaces to form a molten diacetylene monomer layer; applying pressure greater than or equal to about 0.5 psi to the liquid layer disposed between the two opposed surfaces; crystallizing the liquid layer disposed between the two opposed surface, while the liquid layer is kept under constant pressure of at least 0.5 psi, by cooling the molten diacetylene monomer layer at a cooling rate less than or equal to about 0.1° C./minute to form thin large-area single crystal of diacetylene monomer; and exposing the thin large-area single crystal of diacetylene monomer to ultraviolet or gamma radiation to form a thin large-area single crystal of polydiacetylene; wherein the steps of forming, applying pressure to, and crystallizing the liquid layer and exposing the monomer to radiation are all carried out in an inert atmosphere.