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1,2-Bis[5-(4-cyano-phen-yl)-2-methyl-3-thien-yl]-3,3,4,4,5,5-hexa-fluoro-cyclo-pent-1-ene: a photochromic diaryl-ethene compound.

ABSTRACT: The mol-ecules of the title compound, C(29)H(16)F(6)N(2)S(2), a photochromic dithienylethene with 4-cyano-phenyl substituents, adopt an anti-parallel arrangement that is reponsible for photoactivity. The mol-ecule lies on a twofold rotation axis. The dihedral angle between the nearly planar cyclo-pentenyl and heteroaryl rings is 142.5?(3)°, and that between the heteroaryl and benzene rings is 22.4?(3)°. The distance between the heteroaryl rings of adjacent mol-ecules is 3.601?(2)?Å, indicating a ?-? interaction.

SUBMITTER: Liu G

PROVIDER: S-EPMC2961168 | biostudies-literature | 2008 Apr

REPOSITORIES: biostudies-literature

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1,2-Bis[5-(4-cyano-phen-yl)-2-methyl-3-thien-yl]-3,3,4,4,5,5-hexa-fluoro-cyclo-pent-1-ene: a photochromic diaryl-ethene compound.

Liu Gang G Tu Qidong Q Zhang Qing Q Fan Congbin C Yang Tianshe T

Acta crystallographica. Section E, Structure reports online 20080430 Pt 5

The mol-ecules of the title compound, C(29)H(16)F(6)N(2)S(2), a photochromic dithienylethene with 4-cyano-phenyl substituents, adopt an anti-parallel arrangement that is reponsible for photoactivity. The mol-ecule lies on a twofold rotation axis. The dihedral angle between the nearly planar cyclo-pentenyl and heteroaryl rings is 142.5 (3)°, and that between the heteroaryl and benzene rings is 22.4 (3)°. The distance between the heteroaryl rings of adjacent mol-ecules is 3.601 (2) Å, indicating a ...[more]

PMID: 21202419

Similar Datasets

1-(2-Chloro-phen-yl)-2-(2-methyl-5-phenyl-3-thien-yl)-3,3,4,4,5,5-hexa-fluoro-cyclo-pent-1-ene: a new photochromic diaryl-ethene.

Project description:The title compound, C(22)H(13)ClF(6)S, is a hybrid diaryl-ethene derivative with one 3-thienyl substituent, and a Cl-substituted six-membered aryl unit bonded to the double bond of a hexa-fluoro-cyclo-pentene ring. In the crystal structure, the mol-ecule adopts a photo-active anti-parallel conformation that can undergo effective photocyclization reactions. The distance between the two reactive C atoms is 3.848?(3)?Å. The dihedral angles between the least-squares cyclo-pentene plane and those of the adjacent thio-phene and chloro-phenyl rings are 49.39?(8) and 59.88?(8)°, respectively. The F atoms are disordered over two positions, with site occupancy factors of 0.6 and 0.4.

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1,2-Bis[5-(2,2'-dicyano-vinyl)-2-n-pentyl-3-thien-yl]-3,3,4,4,5,5-hexa-fluoro-cyclo-pent-1-ene: a new photochromic diaryl-ethene compound.

Project description:The title compound, C(31)H(26)F(6)N(4)S(2), is a new photochromic dithienylethene with dicyano-vinyl subsitituents. In the crystal structure, the mol-ecule adopts a photoactive anti-parallel conformation, with two n-pentyl groups located on opposite sides of the cyclo-pentene ring. The cyclo-pentene ring assumes an envelope conformation. The distance between the two reactive C atoms on the thio-phene rings is 3.834?(7)?Å. One of the n-pentyl groups is disordered over two positions; the site occupancy factors are ca 0.7 and 0.3.

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1-[5-(3-Chloro-phen-yl)-2-methyl-3-thi-en-yl]-3,3,4,4,5,5-hexa-fluoro-2-(2-methoxy-phen-yl)-cyclo-pent-1-ene.

Project description:The title compound, C(23)H(15)ClF(6)OS, has thienyl and phenyl-ene substituents on the double-bond C atoms of the envelope-shaped cyclo-pentenyl ring. The aromatic systems are aligned at 55.3?(4) (thien-yl) and 60.8?(7)° (phenyl-ene) with respect to the planar C-C=C-C portion of the main central cyclo-pentenyl ring.

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3-(4-{3,3,4,4,5,5-Hexafluoro-2-[5-(3-methoxy-phen-yl)-2-methyl-3-thien-yl]cyclo-pent-1-en-yl}-5-methyl-2-thien-yl)benzonitrile.

Project description:The title compound, C(29)H(19)F(6)NOS(2), is a new unsymmetrical photochromic diarylethene derivative with different meta-phenyl substituents. The distance between the two reactive (i.e. can be irradiated to form a new chemical bond) C atoms is 3.501?(4)?Å; the dihedral angles between the mean plane of the main central cyclo-pentene ring and the thio-phene rings are 47.7?(5) and 45.1?(2)°, and those between the thio-phene rings and the adjacent benzene rings are 29.4?(2) and 28.4?(3)°. The three C atoms and the F atoms of hexa-fuorocyclo-pentene ring are disordered over two positions, with site-occupancy factors of 0.751?(4) and 0.249?(4).

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2-(1,2-Dimethyl-1H-indol-3-yl)-1-{5-[3-(1,3-dioxolan-2-yl)phen-yl]-2-methyl-thio-phen-3-yl}-3,3,4,4,5,5-hexa-fluoro-cyclo-pent-1-ene.

Project description:The title compound, C(29)H(23)F(6)NO(2)S, a member of a new family of photochromic diaryl-ethene compounds having an unsymmetrically substituted hexa-fluoro-cyclo-pentene unit, displays dihedral angles between the indole and thio-phene rings of 52.5?(4)°, and between the indole ring and the planar C-C=C-C unit of the cyclopentene ring of 53.8?(6)°. The distance between the potentially reactive C atoms from the two heteroaryl substituents of 3.817?(6)?Å is proven to be short enough for photocyclization to occur.

| S-EPMC3247444 | biostudies-literature

4-(5-{2-[5-(4-Cyano-phen-yl)-3-methyl-thio-phen-2-yl]-3,3,4,4,5,5-hexa-fluoro-cyclo-pent-1-en-1-yl}-4-methyl-thio-phen-2-yl)benzo-nitrile chloro-form hemisolvate.

Project description:The crystal structure of the title compound, C29H16F6N2S2·0.5CHCl3, consists of mol-ecules with disordered perfluoro-cyclo-pentene rings [occupancy ratio 0.685?(3):0.315?(3)] and close F?F contacts (in the range 2.45-2.73?Å) between mol-ecules. The short contacts are associated with the disorder. The dihedral angle between thiophene rings is 57.44?(8)°. The 5-(4-cyano-phen-yl)-3-methyl-2-thienyl groups of adjacent mol-ecules are parallel, leading to zigzag chains of mol-ecules along [101]. The dihedral angles between each thiophene ring and its adjacent cyanobenzene ring are 8.9?(2) and 7.15?(10)°.

| S-EPMC3772474 | biostudies-literature

Bis(2-thien-yl)acetyl-ene.

Project description:The planar [maximum deviation 0.0066?(4)?Å] symmetrical mol-ecule of the title compound, C(10)H(6)S(2), lies across a crystallographic inversion centre. The thio-phene rings are rotationally disordered about the acetyl-ene bond, with the two pseudo inversion-related S atoms in 0.80:0.20 occupancy sites. The C C bond distance is 1.195?(9)?Å.

| S-EPMC2970215 | biostudies-literature

3,3,4,4,5,5-Hexafluoro-1,2-bis-(5-formyl-2-methylsulfanyl-3-thienyl)cyclo-pent-1-ene.

Project description:In the crystal structure of the title diaryl-ethyl-ene compound, C(17)H(10)F(6)O(2)S(4), the two 3-thienyl substituents are aligned at 44.9?(1) and 40.2?(1)° with respect to the -C-C=C-C- fragment of the central cyclo-pentenyl ring. The five-membered cyclo-pentenyl ring adopts an envelope conformation. The flap atom of this ring and the two F atoms bonded to it are disordered over two positions with occupancies 0.810?(5)/0.190?(5).

| S-EPMC2961574 | biostudies-literature

5-n-Butyl-4-[2-(2-ethyl-1-benzothio-phen-3-yl)-3,3,4,4,5,5-hexa-fluoro-cyclo-pent-1-en-1-yl]thio-phene-2-carbaldehyde.

Project description:The title compound, C(24)H(20)F(6)OS(2), exhibiting photochromic behaviour, has thienyl and benzothienyl substituents attached to the double-bond C atoms of the envelope-shaped cyclo-pentene ring. The mean planes of aromatic systems form dihedral angles of 43.0 (1) (thien-yl) and 73.8 (1)° (benzothien-yl) with the mean plane of the C-C=C-C portion of the cyclo-pentene ring. This conformation avoids steric hindrance between the n-butyl and ethyl substituents. The formyl substituent of the thienyl group, as well as the ethyl substituent of the benzothienyl group, are disordered [occupancies of 0.788 (17):0.212 (17) and 0.64 (5):0.36 (5), respectively].

| S-EPMC2959974 | biostudies-literature

4-{2-[5-(3,5-Difluoro-phen-yl)-2-methyl-thio-phen-3-yl]-3,3,4,4,5,5-hexa-fluoro-cyclo-pent-1-en-1-yl}-1,5-dimethyl-pyrrole-2-carbonitrile.

Project description:In the title compound, C(23)H(14)F(8)N(2)S, the dihedral angles between the pyrrole and thio-phene groups and the almost planar C-C=C-C unit of the cyclo-pentene ring (r.m.s. deviation = 0.4193?Å) are 43.6?(5) and 50.1?(2)°, respectively. The distance of 3.612?(3)?Å between the potentially reactive C atoms of the two heteroaryl substituents is short enough to enable a photocyclization reaction.

| S-EPMC3099757 | biostudies-literature

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