DSC Investigation on anthracene derivative photodimers

Abstract

Anthracene derivative dimers reveal a thermal monomerization at temperatures higher than the melting points of the corresponding monomers. Thermograms of these dimers are consisting of a broad endotherm followed by a small exotherm. A detailed investigation on 9-chloroanthracene dimer allowed to explain this peculiar behaviour.

Synthesis and evaluation of 9-substituted anthracenes with potential in reversible polymer systems

“…9 Hz, 4H, SCH 2 CH 2 OH), 3.72 (t, J=5. 9 Hz, 4H, SCH 2 CH 2 OH), 3.71+4.4 (s, 2H, CCHC), 5.12-5.28 (m, 4H, CCH 2 O), 6.81-7.14 (m, 16H, CCHCHCHCHC); 13 (11-((2,3 -dihydroxypropyl) thio) undecanoate ( (21) 2 ) A dimer of anthracen-9-ylmethyl undec-10-enoate (3) 2 (7.25 g, 9.5 mmol, 1 eq) was dissolved in a minimal amount of tetrahydrofuran (20 mL). 8.2 mL thioglycerol (95 mmol, 5 eq) and 487 mg DMPA (0.9 mmol, 0.1 eq) was added.…”

“…The combined organic phases were dried over magnesium sulfate and the filtrate was concentrated in vacuo. Recrystallization in THF/water was required to obtain (21) 2 as a white solid (7.88 g, 83 %); Mp = 129.5 -134.5 °C; R f (CHCl 3 ) 0; 1 H-NMR (400 MHz, CDCl 3 ): δ (ppm) = 1.13-1.95 (m, 32H, CH 2 CH 2 CH 2 ), 2.18 (m, 3H, CH 2 CH 2 CO(ht)), 2.53-2.89 (m, 9H, CH 2 SCH 2 +CH 2 CH 2 CO(hh)), 3.57-3.83 (m, 7.5H, CHCH 2 OH+ CCHC(ht)), 4.48 (s, 0.5H, CCHC(hh), 5.12-5.27 (m, 4H, CCH 2 O), 6.81-7.12 (m, 16H, CCHCHCHCHC); 13 …”

“…12 Moreover, thermodynamic data are mostly limited to the dimer dissociation enthalpy of a few nonfunctional 9-substituted anthracene dimers that cannot be used for the synthesis of linear or crosslinked polymer systems. 13 In this paper, the synthesis of a series of anthracene derivatives and their corresponding dimers, substituted at the 9-position with moieties having a different degree of M A N U S C R I P T A C C E P T E D ACCEPTED MANUSCRIPT Tetrahedron 2 electronegativity, is described with the aim to understand the relationship between the (photo)chemical properties of these structures and their chemical structure. Each derivative is subsequently spectroscopically characterized with regard to absorption and fluorescence emission in chloroform, acetonitrile and ethanol.…”

Ionization of Anthracene Followed by Fusion in the Solid Phase under Intense Nonresonant Femtosecond Laser Fields

“…The possibility of dianthracene (anthracene photodimer) was excluded because of its small enthalpy of dissociation (0.30 eV). 45 We cannot determine the precise mass of the dimer cation due to low resolution; therefore, the dimer cation would not necessarily be C 28 H 20 , but would be at least C 28 H m . The candidates would be linked cations such as bianthracene (2H loss) and/or fused cations such as dibenzoperylene (4H loss) and phenanthroperylene (6H loss) produced by coalescence 46 as shown in Figure 5.…”