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Pentacene derivative/DTTCNQ cocrystals: alkyl-confined mixed heterojunctions with molecular alignment and transport property tuning.

ABSTRACT: Organic cocrystals are formed via the self-assembly of donor and acceptor constituents, which are mixed together through weak noncovalent interactions. Although they reveal unique physical features, their synthesis still faces major drawbacks for the introduction of more potential semiconductors. Herein, we first report soluble pentacene derivative (TMTES-P) based complexes, with suitable alkyl terminal groups, enabling the location of 4,8-bis(dicyanomethylene)-4,8-dihydrobenzo[1,2-b:4,5-b']-dithiophene (DTTCNQ) in the crystal lattice, thereby allowing the cocrystallization of a binary system on demand. To our surprise, via varying growth conditions, molecular disorders could be removed due to existing short-contacts as the locking force, and even the carrier charge could be changed. This organic donor-acceptor system presents unconventional insights: charge polarity control over (opto)electronic devices with a supramolecular driving force as the directional alignment guide.

SUBMITTER: Ma Y

PROVIDER: S-EPMC7069240 | biostudies-literature | 2019 Dec

REPOSITORIES: biostudies-literature

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Pentacene derivative/DTTCNQ cocrystals: alkyl-confined mixed heterojunctions with molecular alignment and transport property tuning.

Ma Yudong Y Zhou Yecheng Y Jin Jianqun J Wang Wei W Liu Xitong X Xu Haixiao H Zhang Jing J Huang Wei W

Chemical science 20191014 48

Organic cocrystals are formed <i>via</i> the self-assembly of donor and acceptor constituents, which are mixed together through weak noncovalent interactions. Although they reveal unique physical features, their synthesis still faces major drawbacks for the introduction of more potential semiconductors. Herein, we first report soluble pentacene derivative (TMTES-P) based complexes, with suitable alkyl terminal groups, enabling the location of 4,8-bis(dicyanomethylene)-4,8-dihydrobenzo[1,2-<i>b</ ...[more]

PMID: 32206261

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Project description:Leishmaniasis is a neglected parasitic tropical disease with numerous clinical manifestations. One of the causative agents of cutaneous leishmaniasis (CL) is Leishmania tropica (L. tropica) known for causing ulcerative lesions on the skin. The adverse effects of the recommended available drugs, such as amphotericin B and pentavalent antimonial, and the emergence of drug resistance in parasites, mean the search for new safe and effective anti-leishmanial agents is crucial. Miltefosine (MIL) was the first recommended oral medication, but its use is now limited because of the rapid emergence of resistance. Pharmaceutical cocrystallization is an effective method to improve the physicochemical and biological properties of active pharmaceutical ingredients (APIs). Herein, we describe the cocrystallization of coumarin-3-carboxylic acid (CU, 1a; 2-oxobenzopyrane-3-carboxylic acid, C10H6O4) with five coformers [2-amino-3-bromopyridine (1b), 2-amino-5-(trifluoromethyl)-pyridine (1c), 2-amino-6-methylpyridine (1d), p-aminobenzoic acid (1e) and amitrole (1f)] in a 1:1 stoichiometric ratio via the neat grinding method. The cocrystals 2-6 obtained were characterized via single-crystal X-ray diffraction, powder X-ray diffraction, differential scanning calorimetry and thermogravimetric analysis, as well as Fourier transform infrared spectroscopy. Non-covalent interactions, such as van der Waals, hydrogen bonding, C-H...π and π...π interactions contribute significantly towards the packing of a crystal structure and alter the physicochemical and biological activity of CU. In this research, newly synthesized cocrystals were evaluated for their anti-leishmanial activity against the MIL-resistant L. tropica and cytotoxicity against the 3T3 (normal fibroblast) cell line. Among the non-cytotoxic cocrystals synthesized (2-6), CU:1b (2, IC50 = 61.83 ± 0.59 µM), CU:1c (3, 125.7 ± 1.15 µM) and CU:1d (4, 48.71 ± 0.75 µM) appeared to be potent anti-leishmanial agents and showed several-fold more anti-leishmanial potential than the tested standard drug (MIL, IC50 = 169.55 ± 0.078 µM). The results indicate that cocrystals 2-4 are promising anti-leishmanial agents which require further exploration.

Dataset Information

Pentacene derivative/DTTCNQ cocrystals: alkyl-confined mixed heterojunctions with molecular alignment and transport property tuning.

Publications

Pentacene derivative/DTTCNQ cocrystals: alkyl-confined mixed heterojunctions with molecular alignment and transport property tuning.

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