Time-Dependent Solid State Polymorphism of a Series of Donor-Acceptor Dyads

Overview

Journal Cryst Growth Des

Publisher American Chemical Society

Date 2014 Mar 29

PMID 24678269

Citations 2

Authors

Cameron Peebles

Paul M Alvey

Vincent Lynch

Brent L Iverson

Affiliations

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Abstract

In order to exploit the use of favorable electrostatic interactions between aromatic units in directing the assembly of donor-acceptor (D-A) dyads, the present work examines the ability of conjugated aromatic D-A dyads with symmetric side chains to exhibit solid-state polymorphism as a function of time during the solid formation process. Four such dyads were synthesized and their packing in the solid-state from either slower (10-20 days) or faster (1-2 days) evaporation from solvent was investigated using single crystal X-ray analysis and powder X-ray diffraction. Two of the dyads exhibited tail-to-tail (A-A) packing upon slower evaporation from solvent and head-to-tail (D-A) packing upon faster evaporation from solvent. A combination of single crystal analysis and XRD patterns were used to create models wherein a packing model for the other two dyads is proposed. Our findings suggest that while side chain interactions in asymmetric aromatic dyads can play an important role in enforcing segregated D-A dyad assembly, slowly evaporating symmetrically substituted aromatic dyads allows for favorable electrostatic interactions between the aromatic moieties to facilitate the organization of the dyads in the solid-state.

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References

Treier M, Liscio A, Mativetsky J, Kastler M, Mullen K, Palermo V . Photoconductive and supramolecularly engineered organic field-effect transistors based on fibres from donor-acceptor dyads. Nanoscale. 2012; 4(5):1677-81. DOI: 10.1039/c2nr11635a. View

Bandela A, Chinta J, Hinge V, Dikundwar A, Guru Row T, Rao C . Recognition of polycyclic aromatic hydrocarbons and their derivatives by the 1,3-dinaphthalimide conjugate of calix[4]arene: emission, absorption, crystal structures, and computational studies. J Org Chem. 2011; 76(6):1742-50. DOI: 10.1021/jo1023409. View

Wang S, Dossel L, Mavrinskiy A, Gao P, Feng X, Pisula W . Self-assembly and microstructural control of a hexa-peri-hexabenzocoronene-perylene diimide dyad by solvent vapor diffusion. Small. 2011; 7(20):2841-6. DOI: 10.1002/smll.201100730. View

Ringer A, Sinnokrot M, Lively R, Sherrill C . The effect of multiple substituents on sandwich and T-shaped pi-pi interactions. Chemistry. 2006; 12(14):3821-8. DOI: 10.1002/chem.200501316. View

Shao H, Nguyen T, Romano N, Modarelli D, Parquette J . Self-assembly of 1-D n-type nanostructures based on naphthalene diimide-appended dipeptides. J Am Chem Soc. 2009; 131(45):16374-6. DOI: 10.1021/ja906377q. View

Vignon S, Jarrosson T, Iijima T, Tseng H, Sanders J, Stoddart J . Switchable neutral bistable rotaxanes. J Am Chem Soc. 2004; 126(32):9884-5. DOI: 10.1021/ja048080k. View

Benanti T, Saejueng P, Venkataraman D . Segregated assemblies in bridged electron-rich and electron-poor pi-conjugated moieties. Chem Commun (Camb). 2007; (7):692-4. DOI: 10.1039/b610565c. View

Au-Yeung H, Pantos G, Sanders J . Molecular recognition and self-assembly special feature: Dynamic combinatorial synthesis of a catenane based on donor-acceptor interactions in water. Proc Natl Acad Sci U S A. 2009; 106(26):10466-70. PMC: 2705551. DOI: 10.1073/pnas.0809934106. View

Dossel L, Kamm V, Howard I, Laquai F, Pisula W, Feng X . Synthesis and controlled self-assembly of covalently linked hexa-peri-hexabenzocoronene/perylene diimide dyads as models to study fundamental energy and electron transfer processes. J Am Chem Soc. 2012; 134(13):5876-86. DOI: 10.1021/ja211504a. View

10.

Molla M, Das A, Ghosh S . Self-sorted assembly in a mixture of donor and acceptor chromophores. Chemistry. 2010; 16(33):10084-93. DOI: 10.1002/chem.201000596. View

11.

Arnstein S, Sherrill C . Substituent effects in parallel-displaced pi-pi interactions. Phys Chem Chem Phys. 2008; 10(19):2646-55. DOI: 10.1039/b718742d. View

12.

Bredas J, Norton J, Cornil J, Coropceanu V . Molecular understanding of organic solar cells: the challenges. Acc Chem Res. 2009; 42(11):1691-9. DOI: 10.1021/ar900099h. View

13.

Cougnon F, Au-Yeung H, Pantos G, Sanders J . Exploring the formation pathways of donor-acceptor catenanes in aqueous dynamic combinatorial libraries. J Am Chem Soc. 2011; 133(9):3198-207. DOI: 10.1021/ja111407m. View

14.

Lee E, Kim D, Jurecka P, Tarakeshwar P, Hobza P, Kim K . Understanding of assembly phenomena by aromatic-aromatic interactions: benzene dimer and the substituted systems. J Phys Chem A. 2007; 111(18):3446-57. DOI: 10.1021/jp068635t. View

15.

Wheeler S, McNeil A, Muller P, Swager T, Houk K . Probing substituent effects in aryl-aryl interactions using stereoselective Diels-Alder cycloadditions. J Am Chem Soc. 2010; 132(10):3304-11. PMC: 2838923. DOI: 10.1021/ja903653j. View

16.

Ma J, Zhao J, Yang P, Huang D, Zhang C, Li Q . New excited state intramolecular proton transfer (ESIPT) dyes based on naphthalimide and observation of long-lived triplet excited states. Chem Commun (Camb). 2012; 48(78):9720-2. DOI: 10.1039/c2cc35210a. View

17.

Wurthner F, Chen Z, Hoeben F, Osswald P, You C, Jonkheijm P . Supramolecular p-n-heterojunctions by co-self-organization of oligo(p-phenylene vinylene) and perylene bisimide dyes. J Am Chem Soc. 2004; 126(34):10611-8. DOI: 10.1021/ja0475353. View

18.

Gardner R, McKay S, Gellman S . Solvent-dependent stabilization of the E configuration of propargylic secondary amides. Org Lett. 2000; 2(15):2335-8. DOI: 10.1021/ol006096j. View

19.

Yamamoto Y, Zhang G, Jin W, Fukushima T, Ishii N, Saeki A . Ambipolar-transporting coaxial nanotubes with a tailored molecular graphene-fullerene heterojunction. Proc Natl Acad Sci U S A. 2009; 106(50):21051-6. PMC: 2795534. DOI: 10.1073/pnas.0905655106. View

20.

Wheeler S . Local nature of substituent effects in stacking interactions. J Am Chem Soc. 2011; 133(26):10262-74. DOI: 10.1021/ja202932e. View