1,4-Di-9-anthrylbutane

Arslan, Mustafa; Asker, Erol; Masnovi, John; Baker, Ronald J.

doi:10.1107/s1600536807015796

Cited by 2 publications

(7 citation statements)

References 9 publications

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“…The molecular structures of 11 and 13 in the crystalline state are shown in Figure for comparison (see Figure S34, SI for solid state structure of 12 ). All structural parameters of 11 and 13 are in good agreement with the values of the non‐chlorinated derivatives, crystallized by Arslan and co‐workers ,. Compared to each other, no differences within experimental error can be observed for the anthracene skeletons, solely for the C(10)−CH 2 −CH 2 bond angle [115.2(2)° for 11 and 113.9(1)° for 13 ].…”

Section: Resultssupporting

confidence: 77%

“…All structural parameters of 11 and 13 are in good agreement with the values of the nonchlorinated derivatives, crystallized by Arslan and coworkers. [18,19] Compared to each other, no differences within experimental error can be observed for the anthracene skeletons, solely for the C(10)À CH 2 (13, below) in the crystalline state. Displacement ellipsoids are drawn at 50 % probability level.…”

Section: Methodsmentioning

confidence: 92%

“…The intramolecular distances between Sn(1) and Sn(2) as well as Sn (3) and Sn(4) range from 5.4 to 6.0 Å. The coordination sphere of the tin atoms is distorted from local threefold symmetry, most significantly demonstrated for compound 22 by the bond angles C(16)À Sn(1)À C(17) [101.6(1)°] and C(17)À Sn(1)À C (19) [117.0(1)°]. Repulsive interactions between the bulky Me 3 Sngroups are indicated by the torsion angles Sn(1)À C(1)À C(5)À Sn (2) and Sn(3)À C(25)À C(29)À Sn(4) ranging from � 11°to 13°and by a considerable bending of the alkynyl-groups.…”

Section: Photo-cyclomerizing Reactionsmentioning

confidence: 99%

“…Bis{1,8-bis[(trimethylsilyl)ethynyl]anthracen-10-yl}propane(18): Synthesis according to the general procedure for Kumada cross-coupling reactions using 1,3-bis(1,8-dichloroanthracen-10-yl)propane (11; 218 mg, 0.41 mmol), PPh3 and Ni(acac)2 (one spatula tip of each compound), reflux for 3 d. Column chromatography [∅ = 3 cm, l = 9 cm, eluent: n-pentane/dichloromethane(8 : 1)] afforded 18 as bright yellow solid. R f = 0.1 [n-pentane/dichloromethane (8 : 1)].…”

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confidence: 99%

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A Rational Approach to Tetra‐Functional Photo‐Switches

et al. 2019

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α,ω‐Bis(1,8‐dichloroanthracen‐10‐yl)alkanes with (CH 2 ) n ‐linker units ( n =1–4) were synthesized starting from 1,8‐dichloroanthracen‐10(9 H )‐one. This was transformed into anthracenes with allyl, bromomethyl and propargyl substituents in position 10; these were converted in various C−C‐bond formation reactions (plus hydrogenation), leading to two anthracene units flexibly linked by α,ω‐alkandiyl groups. 1,2‐Ethandiyl‐ and 1,3‐propandiyl‐linked derivatives were functionalized with ethynyl groups in positions 1, 8, 1’ and 8’, and these terminally functionalized by Me 3 Sn groups using Me 2 NSnMe 3 . All linked bisanthracenes were subjected to UV light induced cyclomerization and a series of 9,10 : 9’,10’‐photo‐cyclomers were obtained. Their thermal cycloreversion and (repeated) switchability was demonstrated. 1,3‐Bis{1,8‐bis[(trimethylstannyl)ethynyl]anthracen‐10‐yl}propane served as model compound for photo‐switchable acceptor molecules and its open and closed forms were characterized by NMR and DOSY experiments.

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Section: Resultssupporting

confidence: 77%

Section: Methodsmentioning

confidence: 92%

Section: Photo-cyclomerizing Reactionsmentioning

confidence: 99%

mentioning

confidence: 99%

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A Rational Approach to Tetra‐Functional Photo‐Switches

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“…The dianthracenylalkanes were prepared according to literature procedures, and the structures were confirmed by single‐crystal X‐ray diffraction 38–41. Anthracene (zone refined) and 9‐methylanthracene were purchased from Aldrich and recrystallized from ethanol.…”

Section: Methodsmentioning

confidence: 99%

Gaseous cation chemistry and chain‐length effects in electron ionization and collision‐induced dissociation mass spectraof symmetric 1,n‐bis(9‐anthracenyl)alkanes

Schildcrout

Masnovi

2011

J. Mass Spectrom.

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The behavior of the gaseous cations resulting from EI (30 and 70 eV) of the bichromophoric title compounds 1-5 (for n = 1-5, respectively) is examined by ion-trap mass spectrometry, including collision-induced dissociation (CID) with variation in collision energy. These results are compared with those from anthracene and 9-methylanthracene and with previously reported mass spectrometric results for 3 and dicarbazolylalkanes. Rather than using the kinetic method to obtain ion energetics where the fragmentation mechanism is clear, as commonly done, the method is used here with relative complementary-ion abundances from CID to test the proposed fragmentation mechanisms using B3LYP calculations of relative ionization energies and optimized geometries of ionic and neutral fragments. Hydrogen migrations are common, and skeletal rearrangements including formation of expanded, fused and spiro rings are proposed in several cases. Of the chain cleavages, α-homolysis giving C(15) H(11) (+) , likely as dibenzotropylium, is most important for each of 1-5 except 3, where β-cleavage to C(16) H(13) (+) dominates with a proposed methyldibenzotropylium structure. α-Cleavage was important also in the dicarbazolylalkanes. A previous inference of a McLafferty rearrangement to explain C(15) H(12) (+•) from 3 is not supported by the present results. The fragmentation behavior of 1-5 depends strongly on n and implies significant interchromophoric interaction between anthracenyl groups.

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1,4-Di-9-anthrylbutane

Abstract: In the title compound, C32H26, the molecule has an inversion centre at the mid‐point of the central C—C bond. Weak intermolecular C—H...π interactions help to stabilize the crystal structure.

Cited by 2 publications

References 9 publications

A Rational Approach to Tetra‐Functional Photo‐Switches

A Rational Approach to Tetra‐Functional Photo‐Switches

Gaseous cation chemistry and chain‐length effects in electron ionization and collision‐induced dissociation mass spectraof symmetric 1,n‐bis(9‐anthracenyl)alkanes

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