Crystal Engineering of Dual Channel p/n Organic Semiconductors by Complementary Hydrogen Bonding

2014 ◽  
Vol 126 (8) ◽  
pp. 2170-2174 ◽  
Author(s):  
Hayden T. Black ◽  
Dmitrii F. Perepichka
Keyword(s):  
Hydrogen Bonding ◽  
Organic Semiconductors ◽  
Crystal Engineering ◽  
Dual Channel

Supramolecular control of organic p/n-heterojunctions by complementary hydrogen bonding

2014 ◽  
Vol 174 ◽  
pp. 297-312 ◽  
Author(s):  
Hayden T. Black ◽  
Huaping Lin ◽  
Francine Bélanger-Gariépy ◽  
Dmitrii F. Perepichka
Keyword(s):  
Hydrogen Bonding ◽  
Solid State ◽  
Organic Semiconductors ◽  
Crystal Engineering ◽  
Self Assembly ◽  
Structural Control ◽  
Molecular Structures ◽  
Mutual Arrangement ◽  
Donor And Acceptor ◽  
Donor Acceptor

The supramolecular structure of organic semiconductors (OSCs) is the key parameter controlling their performance in organic electronic devices, and thus methods for controlling their self-assembly in the solid state are of the upmost importance. Recently, we have demonstrated the co-assembly of p- and n-type organic semiconductors through a three-point hydrogen-bonding interaction, utilizing an electron-rich dipyrrolopyridine (P2P) heterocycle which is complementary to naphthalenediimides (NDIs) both in its electronic structure and H bonding motif. The hydrogen-bonding-mediated co-assembly between P2P donor and NDI acceptor leads to ambipolar co-crystals and provides unique structural control over their solid-state packing characteristics. In this paper we expand our discussion on the crystal engineering aspects of H bonded donor–acceptor assemblies, reporting three new single co-crystal X-ray diffraction structures and analyzing the different packing characteristics that arise from the molecular structures employed. Particular attention is given toward understanding the formation of the two general motifs observed, segregated and mixed stacks. Co-assembly of the donor and acceptor components into a single, crystalline material, allows the creation of ambipolar semiconductors where the mutual arrangement of p- and n-conductive channels is engineered by supramolecular design based on complementary H bonding.

Concomitant polymorphs of 1,3-bis(3-fluorophenyl)urea

2016 ◽  
Vol 72 (9) ◽  
pp. 692-696 ◽  
Author(s):  
Christina A. Capacci-Daniel ◽  
Jeffery A. Bertke ◽  
Shoaleh Dehghan ◽  
Rupa Hiremath-Darji ◽  
Jennifer A. Swift
Keyword(s):  
Hydrogen Bonding ◽  
Crystal Engineering ◽  
Structural Motif ◽  
Parallel Orientation ◽  
One Dimensional ◽  
Monoclinic Form ◽  
Engineering Studies ◽  
Hydrogen Bonded

Hydrogen bonding between urea functionalities is a common structural motif employed in crystal-engineering studies. Crystallization of 1,3-bis(3-fluorophenyl)urea, C13H10F2N2O, from many solvents yielded concomitant mixtures of at least two polymorphs. In the monoclinic form, one-dimensional chains of hydrogen-bonded urea molecules align in an antiparallel orientation, as is typical of many diphenylureas. In the orthorhombic form, one-dimensional chains of hydrogen-bonded urea molecules have a parallel orientation rarely observed in symmetrically substituted diphenylureas.

Growth direction dependent separate-channel charge transport in organic weak charge-transfer co-crystal of anthracene-DTTCNQ

2022 ◽  
Author(s):  
Hui Jiang ◽  
Jun Ye ◽  
Peng Hu ◽  
Shengli Zhu ◽  
Yanqin Liang ◽  
...  
Keyword(s):  
Charge Transfer ◽  
Charge Transport ◽  
Electronic Properties ◽  
Single Crystals ◽  
Organic Semiconductors ◽  
Crystal Engineering ◽  
Molecular Crystal ◽  
Growth Direction ◽  
Weak Charge ◽  
Separate Channel

Co-crystallization is an efficient way of molecular crystal engineering to tune the electronic properties of organic semiconductors. In this work, we synthesized anthracene-4,8-bis(dicyanomethylene)4,8-dihydrobenzo[1,2-b:4,5-b’]-dithiophene (DTTCNQ) single crystals as a template to...

Crystal Engineering Organic Semiconductors

2011 ◽  
pp. 1-19 ◽  
Author(s):  
Joseph C. Sumrak ◽  
Anatoliy N. Sokolov ◽  
Leonard R. Macgillivray
Keyword(s):  
Organic Semiconductors ◽  
Crystal Engineering

Polysulfonylamine, CXXVI [1] Wasserstoffbrücken in kristallinen Onium-dimesylamiden: Ein robustes Achtring-Synthon in Koexistenz mit einem dritten Wasserstoffbrückenmotiv - Cyclodimere, Ketten, supramolekulare Bindungsisomere und ein fünffach verwobenes dreidimensionales (C-H ∙∙∙ O - Netzwerk / Polysulfonylamines, CXXVI [1] Hydrogen Bonding in Crystalline Onium Dimesylamides: A Robust Eight- Membered Ring Synthon in Coexistence with a Third Hydrogen Bonding Motif - Cyclodimers, Chains, Supramolecular Linkage Isomers, and a Quintuply Interwoven Three-Dimensional C - H ∙∙∙ O Network

2000 ◽  
Vol 55 (8) ◽  
pp. 738-752 ◽  
Author(s):  
Oliver Moers ◽  
Karna Wijaya ◽  
Ilona Lange ◽  
Armand Blaschette ◽  
Peter G. Jones
Keyword(s):  
Hydrogen Bond ◽  
Hydrogen Bonding ◽  
Crystal Engineering ◽  
Ion Pairs ◽  
Three Dimensional ◽  
Membered Ring ◽  
Monoclinic Space Group ◽  
Hydrogen Bond Donor ◽  
Linkage Isomers ◽  
Ionic Solids

As an exercise in crystal engineering, low-temperature X-ray structures were determined for six rationally designed ionic solids of general formula BH+(MeSO2)2N−, where BH+ is 2-aminopyridinium (2, monoclinic, space group P21/c, Z = 4), 2-aminopyrimidinium (3, orthorhombic, Pbca, Z = 8), 2-aminothiazolium (4, orthorhombic, Pbcn, Z = 8), 2-amino-6-methylpyridinium (5, solvated with 0.5 H20, monoclinic, C2/c, Z = 8), 2-amino-1,3,4-thiadiazolium (6, triclinic, P1̄, Z = 2), or 2-amino-4,6-dimethylpyrimidinium (7, orthorhombic. Fdd2, Z = 16). The onium cations in question exhibit a trifunctional hydrogen-bond donor sequence H − N (H*)-C (sp2) − N − H , which is complementary to an O − S (sp3)−N fragment of the anion and simultaneously expected to form a third hydrogen bond via the exocyclic N − H* donor. Consequently, all the crystal packings contain cation-anion pairs assembled by an N − H ∙∙∙ N and an N −H ∙∙∙ O hydrogen bond, these substructures being mutually associated through an N − H* ∙∙∙ O bond. For the robust eight-membered ring synthon within the ion pairs [graph set N2 = R22(8), antidromic], two supramolecular isomers were observed: In 2 and 3, N − H ∙∙∙ N originates from the ring NH donor and N − H ∙∙∙ O from the exocyclic amino group, whereas in 4-7 these connectivities are reversed. The third hydrogen bond, N − H*∙∙∙ O , leads either to chains of ion pairs (generated by a 21 transformation in 2-4 or by a glide plane in 5) or to cyclic dimers of ion pairs (Ci symmetric in 6, C2-symmetric in 7). The overall variety of motifs observed in a small number of structures reflects the limits imposed on the prediction of hydrogen bonding patterns. Owing to the excess of potential acceptors over traditional hydrogen-bond donors, several of the structures display prominent non-classical secondary bonding. Thus, the cyclodimeric units of 6 are associated into strands through short antiparallel O ∙∙∙ S(cation) interactions. In the hemihydrate 5, two independent C-H(cation) ∙∙∙ O bonds generate a second antidromic R22(8) pattern, leading to sheets composed of N − H ∙∙∙ N/O connected catemers; the water molecules are alternately sandwiched between and O - H ∙∙∙ O bonded to the sheets to form bilayers, which are cross-linked by a third C − H (cation ) ∙∙∙ O contact. The roof-shaped cyclodimers occurring in 7 occupy the polar C2 axes parallel to z and build up hollow Car− H ∙∙∙ O bonded tetrahedral lattices; in order to fill their large empty cavities, five translationally equivalent lattices mutually interpenetrate.

Sign in / Sign up

Export Citation Format

Share Document