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A series of DAN as well as NDI building blocks have been examined (wherein the relative distance between the two amide groups in a particular chromophore is the variable structural parameter) to understand the structure\u2010dependent variation in mode of supramolecular assembly and morphology (organogel, reverse vesicle, etc.) of the self\u2010assembled material. Interestingly, it was observed that when the amide functionalities are introduced to enhance the self\u2010assembly propensity, the mode of co\u2010assembly among the DAN and NDI chromophores no longer remained trivial and was dictated by a relatively stronger hydrogen\u2010bonding interaction instead of a weak CT interaction. Consequently, in a highly non\u2010polar solvent like methylcyclohexane (MCH), although kinetically controlled CT\u2010gelation was initially noticed, within a few hours the system sacrificed the CT\u2010interaction and switched over to the more stable self\u2010sorted gel to maximize the gain in enthalpy from the hydrogen\u2010bonding interaction. In contrast, in a relatively less non\u2010polar solvent such as tetrachloroethylene (TCE), in which the strength of hydrogen bonding is inherently weak, the contribution of the CT interaction also had to be accounted for along with hydrogen bonding leading to a stable CT\u2010state in the gel or solution phase. The stability and morphology of the CT complex and rate of supramolecular switching (from CT to segregated state) were found to be greatly influenced by subtle structural variation of the building blocks, solvent polarity, and the DAN\/NDI ratio. For example, in a given D\u2013A pair, by introducing just one methylene unit in the spacer segment of either of the building blocks a complete change in the mode of co\u2010assembly (CT state or segregated state) and the morphology (1D fiber to 2D reverse vesicle) was observed. The role of solvent polarity, structural variation, and D\/A ratio on the nature of co\u2010assembly, morphology, and the unprecedented supramolecular\u2010switching phenomenon have been studied by detail spectroscopic and microscopic experiments in a gel as well as in the solution state and are well supported by DFT calculations.<\/jats:p>","DOI":"10.1002\/chem.201201140","type":"journal-article","created":{"date-parts":[[2012,7,10]],"date-time":"2012-07-10T14:50:38Z","timestamp":1341931838000},"page":"9849-9859","source":"Crossref","is-referenced-by-count":74,"title":["Hydrogen\u2010Bonding Induced Alternate Stacking of Donor (D) and Acceptor (A) Chromophores and their Supramolecular Switching to Segregated States"],"prefix":"10.1002","volume":"18","author":[{"given":"Anindita","family":"Das","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Mijanur 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